A series of dearomatized isoprenylated acylphloroglucinols derivatives,hyperhenols A-E(1-5),as well as seven known analogues(6-12),were characterized from Hypericum henryi.Their structures were determined by combinati...A series of dearomatized isoprenylated acylphloroglucinols derivatives,hyperhenols A-E(1-5),as well as seven known analogues(6-12),were characterized from Hypericum henryi.Their structures were determined by combination of NMR,ECD spectroscopy,and X-ray difraction analysis.Compounds 1 and 6-8 were tested to exhibit potential antitumor properties,of which 6 and 7 inhibited cell growth through inducing apoptosis and cell cycle arrest.In addition,these compounds could induce autophagy and PINK1/Parkin-mediated mitophagy in cancer cell lines,as well as suppress lung cancer A549 cells metastasis in vitro.展开更多
Linear alkyl benzenes (LABs) are the main materials for detergent production. The presence of aromatic compounds in this material can decrease the quality of the final product and enhance the deactivation rate of ca...Linear alkyl benzenes (LABs) are the main materials for detergent production. The presence of aromatic compounds in this material can decrease the quality of the final product and enhance the deactivation rate of catalysts. In this research we used zeolite NaX for de-aromatization of the recycled paraffin from the alkylation unit of an LAB production complex. The effect of different parameters on the removal efficiency of adsorbent was studied and optimized. To study the re-usability of the adsorbent, the breakthrough curves were obtained by using a fixed bed column filled with the adsorbent. The results indicated that the adsorbent capacity remained unchanged after three regeneration cycles. The Langmuir and Freundlich adsorption models were applied to describe the equilibrium isotherms. It was concluded that the Langmuir model agreed well with the experimental data. The calculated thermodynamic parameters of the adsorption showed that the adsorption process was spontaneous and exothermic. The reaction rate was estimated by the pseudo-second order kinetic model.展开更多
Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong backgr...Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder reaction, allowing the implementation of the projected reaction at ambient temperature. Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity. By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio–selectivities(33 examples, up to 97% yield and >99% ee, >20:1 dr).展开更多
Herein,we achieved a green and efficient dearomatization for the synthesis of 2,3-functionalized polycyclic indolines in an electrochemical way.This avoiding of external oxidants and metals approach allowed various nu...Herein,we achieved a green and efficient dearomatization for the synthesis of 2,3-functionalized polycyclic indolines in an electrochemical way.This avoiding of external oxidants and metals approach allowed various nucleophilic sources(Nu¼anilines,TMSN3 and ROH)to perform the products,representing an environmentally benign means.Additionally,the continuous flow electrosynthesis and synthetic transformations also reveal the strong practicality of electrochemistry in organic synthesis.展开更多
Atom-and step-economy in IBX assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary α-amino acid analogs offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocent...Atom-and step-economy in IBX assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary α-amino acid analogs offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocenter in 20%–91% yields under mild conditions via 7,8-dearomatization of quinolines. Free of a preinstalled activation group is highlight of this intramolecular oxidation spiroannulation tandem reaction. This type of N-heterospirocycles, traditionally difficult to access, may open the door to a potentially interest scaffold for synthetic and medicinal chemistry.展开更多
Catalytic asymmetric dearomatization of indoles and alkynes has received much attention in the past decade because this strategy offers an attractive and alternative way for the efficient synthesis of valuable chiral ...Catalytic asymmetric dearomatization of indoles and alkynes has received much attention in the past decade because this strategy offers an attractive and alternative way for the efficient synthesis of valuable chiral polycyclic indolines. However, these reactions have been mostly limited to transition-metal catalysts, and the related chiral Br■nsted acid catalysis has been scarcely reported. Herein, we disclose a chiral phosphoric acid-catalyzed asymmetric dearomatization of indolyl ynamides by direct activation of alkynes. This metal-free method enables the practical and atom-economical construction of an array of valuable chiral polycyclic indolines in moderate to good yields with high enantioselectivities.展开更多
Bichner reaction,as a unique type of expansive dearomatization,has become a practical strategy for the straightforward assembly of valuable functionalized cycloheptatrienes from ubiquitous aromatic precursors.Although...Bichner reaction,as a unique type of expansive dearomatization,has become a practical strategy for the straightforward assembly of valuable functionalized cycloheptatrienes from ubiquitous aromatic precursors.Although the asymmetric version has been investigated since the early 1990s,enantioselective Bichner reaction is still limited by the catalyst type and substrate scope.This review aims to propose the limitation and possible development direction of this field by summarizing the evolution of catalytic asymmetric Bichner reaction,which is organized on the basis of intra-and intermolecular reactions.Considering the different metal carbene precursors,the reactions are further classified by carbene sources.展开更多
Asymmetric dearomatization reactions of various electron-deficient heteroarenes,including benzofurans,benzothiophenes,and indoles,have been described.Through a phosphine-catalyzed[3+2]annulation with vinylcyclopropane...Asymmetric dearomatization reactions of various electron-deficient heteroarenes,including benzofurans,benzothiophenes,and indoles,have been described.Through a phosphine-catalyzed[3+2]annulation with vinylcyclopropanes,readily available heteroarene feedstocks undergo smooth dearomatization reactions,delivering a diverse array of valuable chiral cyclopentabenzodihydrofuran and cyclopentaindoline scaffolds in a highly diastero-and enantioselective manner.Notably,the employment of cyclopropanes in phosphine-mediated annulation for the dearomatization of electron-deficient arenes is unknown.展开更多
A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported.This protocol provides an efficient access for highly congested quaternatry carbon centers con...A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported.This protocol provides an efficient access for highly congested quaternatry carbon centers construction.It also features operationally simplicity,mild reaction conditions and good functional group tolerance.Moreover,the reported procedure can be easily emplified to 1 g scale.Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.展开更多
An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase-transfer catalysis. Vari- ous fluorinated furoindolines were obtained in moderate to excellent yields ...An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase-transfer catalysis. Vari- ous fluorinated furoindolines were obtained in moderate to excellent yields and enantioselectivity in the presence of Selectfluor. The preliminary mecha- nistic studies suggested the existence of an in situ formed tryptophol boronic ester plays a critical role in determining the enantioselectivity. This method features the facile introduction of a fluorine atom in a highly enantioselective manner and construction of two contiguous quaternary stereogenic cen- ters.展开更多
Copper-catalyzed intermolecular oxidative-etherification type dearomatization reaction of 2-naphthols was developed.With air as the terminal oxidant,the reaction proceeded in excellent yields under mild conditions.In ...Copper-catalyzed intermolecular oxidative-etherification type dearomatization reaction of 2-naphthols was developed.With air as the terminal oxidant,the reaction proceeded in excellent yields under mild conditions.In addition,the reaction between two different naphthol substrates occurred smoothly.A series of multifunctionalized β-naphthalenones,important scaffold existed widely in natural products and biologically active molecules,were synthesized efficiently.展开更多
Polycyclic in doli nes and in dole nines were synthesized via base-catalyzed in tramolecular dearomatizi ng 3-alke nylation reacti ons of al-kynyl in doles 1 at room temperature.The base enhan ced the nu cleophilicity...Polycyclic in doli nes and in dole nines were synthesized via base-catalyzed in tramolecular dearomatizi ng 3-alke nylation reacti ons of al-kynyl in doles 1 at room temperature.The base enhan ced the nu cleophilicity of the carb on at the 3-position of the indole moiety,facilitating an exclusive S-exo-dig cyclization reaction with the alkyne to form spiroindolenines2.展开更多
A bicyclo[2.2.2]octane C/D ring system, with a lactonic ring at C-8 and C-9, of the atisine-type C20-diterpenoid alkaloids, was successfully synthesized, using an oxidative dearomatization/intramolecular Diels-Alder r...A bicyclo[2.2.2]octane C/D ring system, with a lactonic ring at C-8 and C-9, of the atisine-type C20-diterpenoid alkaloids, was successfully synthesized, using an oxidative dearomatization/intramolecular Diels-Alder reaction.展开更多
A mild and efficient dearomatic [3+2] annulation reaction of 3-nitro-7-azaindoles and Morita Baylis Hillman carbonates from isatins was developed catalyzed by DMAP, affording the corresponding polycyclic spirooxindol...A mild and efficient dearomatic [3+2] annulation reaction of 3-nitro-7-azaindoles and Morita Baylis Hillman carbonates from isatins was developed catalyzed by DMAP, affording the corresponding polycyclic spirooxindoles containing fused azaindoline architectures and vicinal quaternary centers in excellent yields(up to 96%) with high regio- and diastereoselectivity(dr 〉 19:1). Moderate enantioselectivity(79% ee) was obtained by employing a chiral DMAP-type Lewis base catalyst.展开更多
We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal S...We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal Suzuki coupling procedure.Substrates bearing various functional groups are well tolerated in the reaction,affording the diarylated indoline skeletons in moderate to good yields.展开更多
A visible-light-induced spirocyclizative hydroarylation via reductive dearomatization of a series of non activated arenes including 2-phenyl indoles and naphthalene derivatives under mild conditions is de scribed.An i...A visible-light-induced spirocyclizative hydroarylation via reductive dearomatization of a series of non activated arenes including 2-phenyl indoles and naphthalene derivatives under mild conditions is de scribed.An intriguing chemoselective dearomative hydroarylation of 2-phenyl indoles is presented.Th dearomative hydroarylation protocol rapidly delivers valuable spirocycles with carbon-carbon doub bonds from readily accessible aromatic precursors in a single step.展开更多
Here is an operable and rare strategy for copper-initiated radical dearomative 2,5-alkylarylation of furan. By means of this strategy, we realized the dearomatization of furans to construct spirooxindoles with good yi...Here is an operable and rare strategy for copper-initiated radical dearomative 2,5-alkylarylation of furan. By means of this strategy, we realized the dearomatization of furans to construct spirooxindoles with good yield in one-step via trihalomethylation/spirocyclization cascade progress.展开更多
A mild and practical protocol for selectively time-dependent dehydrogenative C–C coupling,as well as tandem couplingcyclization reaction between indoles or/and other heteroaromatics via electrochemically oxidative pr...A mild and practical protocol for selectively time-dependent dehydrogenative C–C coupling,as well as tandem couplingcyclization reaction between indoles or/and other heteroaromatics via electrochemically oxidative process has been demonstrated.The reaction runs under noble catalyst,external oxidant and inert gas free condition,allowing tunable access to a wide variety of synthetically useful symmetrical or nonsymmetrical heteroarene with aggregation-induced emission(AIE),and polycyclic 3-D indole derivatives with aggregation-caused quenching(ACQ)fluorescence properties.Finally,preliminary mechanistic study indicated that tunable generation of indole cation under various electrolysis potential via regulating Nprotecting group was the key to achieve cross-coupling between indoles and other heteroaromatics.展开更多
The copper-catalyzed directed dearomatization of indoles with the assistance of directing groups has been developed for the synthesis of 2,3-diazido indolines with good yields and excellent diastereoselectivities in a...The copper-catalyzed directed dearomatization of indoles with the assistance of directing groups has been developed for the synthesis of 2,3-diazido indolines with good yields and excellent diastereoselectivities in aqueous solution.The resultant 2,3-diazides can be smoothly converted to other functional groups,including vicinal diamines,triazoles and benzotriazoles,in a single step.展开更多
A catalytic asymmetric hydroxylative dearomatization reaction has been disclosed,and the products can smoothly transform into spiroannulation adducts by simply treated with a base under mild conditions.Novel in-situ g...A catalytic asymmetric hydroxylative dearomatization reaction has been disclosed,and the products can smoothly transform into spiroannulation adducts by simply treated with a base under mild conditions.Novel in-situ generated magnesium catalytic methods are developed by application of combinational ligands.Related concise transformaitons of the spiroannulation adducts have been carried out.展开更多
基金supported by the NSFC-Joint Foundation of Yunnan Province(U1902213)Chongqing Municipal Natural Science Foundation(cstc2018jcyjAX0388)+3 种基金the Second Tibetan Plateau Scientific Expedition and Research(STEP)program(2019QZKK0502)Southeast Asia Biodiversity Research Institute,CAS(2017CASSEABRIQG003)State Key Laboratory of Phytochemistry and Plant Resources in West China(P2017-KF02 and P2019-ZZ05)the Natural Sciences Foundation of Yunnan Province(2019FA003).
文摘A series of dearomatized isoprenylated acylphloroglucinols derivatives,hyperhenols A-E(1-5),as well as seven known analogues(6-12),were characterized from Hypericum henryi.Their structures were determined by combination of NMR,ECD spectroscopy,and X-ray difraction analysis.Compounds 1 and 6-8 were tested to exhibit potential antitumor properties,of which 6 and 7 inhibited cell growth through inducing apoptosis and cell cycle arrest.In addition,these compounds could induce autophagy and PINK1/Parkin-mediated mitophagy in cancer cell lines,as well as suppress lung cancer A549 cells metastasis in vitro.
基金Financial support of the Iran Chemical Industries Investment Company is greatly acknowledged
文摘Linear alkyl benzenes (LABs) are the main materials for detergent production. The presence of aromatic compounds in this material can decrease the quality of the final product and enhance the deactivation rate of catalysts. In this research we used zeolite NaX for de-aromatization of the recycled paraffin from the alkylation unit of an LAB production complex. The effect of different parameters on the removal efficiency of adsorbent was studied and optimized. To study the re-usability of the adsorbent, the breakthrough curves were obtained by using a fixed bed column filled with the adsorbent. The results indicated that the adsorbent capacity remained unchanged after three regeneration cycles. The Langmuir and Freundlich adsorption models were applied to describe the equilibrium isotherms. It was concluded that the Langmuir model agreed well with the experimental data. The calculated thermodynamic parameters of the adsorption showed that the adsorption process was spontaneous and exothermic. The reaction rate was estimated by the pseudo-second order kinetic model.
基金the generous financial support from Natural Science Foundation of Henan Province (No.222300420084)application research plan of Key Scientific Research Projects in Colleges and Universities of Henan Province (No.22A150056)+1 种基金the Youth Innovation Team Program in Colleges and Universities of Shandong Province (No.2022KJ228)National Natural Science Foundation of China (No.22208302)。
文摘Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder reaction, allowing the implementation of the projected reaction at ambient temperature. Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity. By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio–selectivities(33 examples, up to 97% yield and >99% ee, >20:1 dr).
基金We are grateful to the National Natural Science Foundation of China(Nos.21961037,21861036,22161044 and 22201241)the Program for Tianshan Innovative Research Team of Xinjiang Uygur Autonomous Region(No.2021D14011)+1 种基金the Natural Science Foundation of Xinjiang Uygur Autonomous Region(Nos.2020D01C077 and 2021D01E10)the Key Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region(No.2022D01D06)for support of this research。
文摘Herein,we achieved a green and efficient dearomatization for the synthesis of 2,3-functionalized polycyclic indolines in an electrochemical way.This avoiding of external oxidants and metals approach allowed various nucleophilic sources(Nu¼anilines,TMSN3 and ROH)to perform the products,representing an environmentally benign means.Additionally,the continuous flow electrosynthesis and synthetic transformations also reveal the strong practicality of electrochemistry in organic synthesis.
基金the National Natural Science Foundation of China (Nos. 22101074, 21877206, and 21772032)the 111 Project (No. D17007)+2 种基金Excellent Youth Foundation of Henan Scientific Committee (No. 222300420012)China Postdoctoral Science Foundation (No. 2019M660173)the Natural Science Foundation of Henan Province (No. 202300410233)。
文摘Atom-and step-economy in IBX assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary α-amino acid analogs offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocenter in 20%–91% yields under mild conditions via 7,8-dearomatization of quinolines. Free of a preinstalled activation group is highlight of this intramolecular oxidation spiroannulation tandem reaction. This type of N-heterospirocycles, traditionally difficult to access, may open the door to a potentially interest scaffold for synthetic and medicinal chemistry.
基金financial support from the National Natural Science Foundation of China(Nos.22125108,22101238,92056104 and 21772161)the China Postdoctoral Science Foundation(No.2020M680087)+3 种基金the Natural Science Foundation of Fujian Province of China(No.2019J02001)the President Research Funds from Xiamen University(No.20720210002)the Fundamental Research Funds for the Central Universities(No.20720202008)NFFTBS(No.J1310024)。
文摘Catalytic asymmetric dearomatization of indoles and alkynes has received much attention in the past decade because this strategy offers an attractive and alternative way for the efficient synthesis of valuable chiral polycyclic indolines. However, these reactions have been mostly limited to transition-metal catalysts, and the related chiral Br■nsted acid catalysis has been scarcely reported. Herein, we disclose a chiral phosphoric acid-catalyzed asymmetric dearomatization of indolyl ynamides by direct activation of alkynes. This metal-free method enables the practical and atom-economical construction of an array of valuable chiral polycyclic indolines in moderate to good yields with high enantioselectivities.
基金support from MoST(No.2021YFC2100100)the National Natural Science Foundation of China(No.22125108)Yunnan Normal University,and Applied Basic Research Projects of Yunnan Province(No.202101AT070217).
文摘Bichner reaction,as a unique type of expansive dearomatization,has become a practical strategy for the straightforward assembly of valuable functionalized cycloheptatrienes from ubiquitous aromatic precursors.Although the asymmetric version has been investigated since the early 1990s,enantioselective Bichner reaction is still limited by the catalyst type and substrate scope.This review aims to propose the limitation and possible development direction of this field by summarizing the evolution of catalytic asymmetric Bichner reaction,which is organized on the basis of intra-and intermolecular reactions.Considering the different metal carbene precursors,the reactions are further classified by carbene sources.
文摘Asymmetric dearomatization reactions of various electron-deficient heteroarenes,including benzofurans,benzothiophenes,and indoles,have been described.Through a phosphine-catalyzed[3+2]annulation with vinylcyclopropanes,readily available heteroarene feedstocks undergo smooth dearomatization reactions,delivering a diverse array of valuable chiral cyclopentabenzodihydrofuran and cyclopentaindoline scaffolds in a highly diastero-and enantioselective manner.Notably,the employment of cyclopropanes in phosphine-mediated annulation for the dearomatization of electron-deficient arenes is unknown.
基金supported by the“Fundamental Research Funds for the Central Universities”(Nos.21620318 and 2019QNGG22)the“Guangdong Basic and Applied Basic Research Fund”(No.2021A1515012023)“the Open Fund of Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications”(No.2020B121201005).
文摘A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported.This protocol provides an efficient access for highly congested quaternatry carbon centers construction.It also features operationally simplicity,mild reaction conditions and good functional group tolerance.Moreover,the reported procedure can be easily emplified to 1 g scale.Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.
文摘An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase-transfer catalysis. Vari- ous fluorinated furoindolines were obtained in moderate to excellent yields and enantioselectivity in the presence of Selectfluor. The preliminary mecha- nistic studies suggested the existence of an in situ formed tryptophol boronic ester plays a critical role in determining the enantioselectivity. This method features the facile introduction of a fluorine atom in a highly enantioselective manner and construction of two contiguous quaternary stereogenic cen- ters.
文摘Copper-catalyzed intermolecular oxidative-etherification type dearomatization reaction of 2-naphthols was developed.With air as the terminal oxidant,the reaction proceeded in excellent yields under mild conditions.In addition,the reaction between two different naphthol substrates occurred smoothly.A series of multifunctionalized β-naphthalenones,important scaffold existed widely in natural products and biologically active molecules,were synthesized efficiently.
基金This work was supported by grants from the National Program on Key Research Project(No.2016YFA0602900)the National Natural Science Foundation of China(Nos.21572068 and 21871094)+2 种基金the Guangdong Natural Science Foundation(No.2017A030312005)the Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine[(2014)NO.32]the Special Foundation of Guangzhou Key Laboratory(No.202002010004).
文摘Polycyclic in doli nes and in dole nines were synthesized via base-catalyzed in tramolecular dearomatizi ng 3-alke nylation reacti ons of al-kynyl in doles 1 at room temperature.The base enhan ced the nu cleophilicity of the carb on at the 3-position of the indole moiety,facilitating an exclusive S-exo-dig cyclization reaction with the alkyne to form spiroindolenines2.
基金the financial support provided by the National Science Foundation of China(No.81273387)
文摘A bicyclo[2.2.2]octane C/D ring system, with a lactonic ring at C-8 and C-9, of the atisine-type C20-diterpenoid alkaloids, was successfully synthesized, using an oxidative dearomatization/intramolecular Diels-Alder reaction.
基金financial support from the NSFC(21572135 and 21321061)
文摘A mild and efficient dearomatic [3+2] annulation reaction of 3-nitro-7-azaindoles and Morita Baylis Hillman carbonates from isatins was developed catalyzed by DMAP, affording the corresponding polycyclic spirooxindoles containing fused azaindoline architectures and vicinal quaternary centers in excellent yields(up to 96%) with high regio- and diastereoselectivity(dr 〉 19:1). Moderate enantioselectivity(79% ee) was obtained by employing a chiral DMAP-type Lewis base catalyst.
基金the Shanghai Institute of Materia Medicathe Chinese Academy of Sciences+4 种基金the National Natural Science Foundation of China(Nos.21772211 and 21920102003)the Youth Innovation Promotion Association CAS(Nos.2014229 and 2018293)the Science and Technology Commission of Shanghai Municipality(Nos.17JC1405000 and 18431907100)the Program of Shanghai Academic Research Leader(No.19XD1424600)the National Science&Technology Major Project“Key New Drug Creation and Manufacturing Program”,China(No.2018ZX09711002-006)for financial support。
文摘We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal Suzuki coupling procedure.Substrates bearing various functional groups are well tolerated in the reaction,affording the diarylated indoline skeletons in moderate to good yields.
基金the financial supports from the National Natural Science Foundation of China(Nos.22022111,21871257,21801240)the Natural Science Foundation of Fujian Province(No.2020J02008)the Strategic Priority Research Program of the Chinese Academy of Sciences(No.XDB20000000)。
文摘A visible-light-induced spirocyclizative hydroarylation via reductive dearomatization of a series of non activated arenes including 2-phenyl indoles and naphthalene derivatives under mild conditions is de scribed.An intriguing chemoselective dearomative hydroarylation of 2-phenyl indoles is presented.Th dearomative hydroarylation protocol rapidly delivers valuable spirocycles with carbon-carbon doub bonds from readily accessible aromatic precursors in a single step.
基金supported by the National Natural Science Foundation of China(21871094)the Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine[(2014)No.32]We also thank the support of the Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation(No.2021CL04).
文摘Here is an operable and rare strategy for copper-initiated radical dearomative 2,5-alkylarylation of furan. By means of this strategy, we realized the dearomatization of furans to construct spirooxindoles with good yield in one-step via trihalomethylation/spirocyclization cascade progress.
基金supported by Guangdong Basic and Applied Basic Research Foundation (2019A1515011743)the Pearl River talent program of Guangdong Province (Youth Top-Notch Talent,2017GC010302)Jinan University
文摘A mild and practical protocol for selectively time-dependent dehydrogenative C–C coupling,as well as tandem couplingcyclization reaction between indoles or/and other heteroaromatics via electrochemically oxidative process has been demonstrated.The reaction runs under noble catalyst,external oxidant and inert gas free condition,allowing tunable access to a wide variety of synthetically useful symmetrical or nonsymmetrical heteroarene with aggregation-induced emission(AIE),and polycyclic 3-D indole derivatives with aggregation-caused quenching(ACQ)fluorescence properties.Finally,preliminary mechanistic study indicated that tunable generation of indole cation under various electrolysis potential via regulating Nprotecting group was the key to achieve cross-coupling between indoles and other heteroaromatics.
基金the National Natural Science Foundation of China(Nos.21472172,21272212)Natural Science Foundation of Zhejiang Province(No.LY17B060009)。
文摘The copper-catalyzed directed dearomatization of indoles with the assistance of directing groups has been developed for the synthesis of 2,3-diazido indolines with good yields and excellent diastereoselectivities in aqueous solution.The resultant 2,3-diazides can be smoothly converted to other functional groups,including vicinal diamines,triazoles and benzotriazoles,in a single step.
基金the financial support from the National Natural Science Foundation of China (Nos. 21901092, 21807053)Innovation Fund for Medical Sciences (No. 2019-12M-5-074)+2 种基金Program for Chang-jiang Scholars and Innovative Research Team in University (PCSIRT) (No. IRT_15R27)the Funds for Fundamental Research Creative Groups of Gansu Province (No. 20JR5RA310)the Fundamental Research Funds for the Central Universities (Nos. lzujbky2020-49, 2021-kb21)
文摘A catalytic asymmetric hydroxylative dearomatization reaction has been disclosed,and the products can smoothly transform into spiroannulation adducts by simply treated with a base under mild conditions.Novel in-situ generated magnesium catalytic methods are developed by application of combinational ligands.Related concise transformaitons of the spiroannulation adducts have been carried out.