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Synthesis of Symmetrical Biaryls via Rhodium Catalyzed Dimerization of Arylmercurials and Mechanism of the Dimerization 被引量:2
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作者 WANG Yulan WU Yangjie 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2000年第2期131-135,共5页
A series of symmetrical biaryls was synthesized from arylmercuric chlorides and biarylmercurials in the presence of [ClRh(CO) 2] 2 in hexamethylphosphoramide(HMPA). The mechanism of the [ClRh(CO) 2] 2 catalyzed d... A series of symmetrical biaryls was synthesized from arylmercuric chlorides and biarylmercurials in the presence of [ClRh(CO) 2] 2 in hexamethylphosphoramide(HMPA). The mechanism of the [ClRh(CO) 2] 2 catalyzed dimerization of biarylmercurials was studied, and shown to be mainly intermolecular reaction. 展开更多
关键词 Symmetrical biaryls Synthesis Arylmercurials Intermolecular reaction
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An Efficient Palladium-catalyzed Coupling Reaction for the Preparation of Biaryls and Polyaryls
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作者 Zhi Yong WANG Zheng Gen ZHA +1 位作者 Jia Hai ZHANG Ji Hui WU 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第1期13-16,共4页
In the case of Pd(PPh3)4 as catalyst and toluene as reaction solvent, the desired biaryls and polyaryls were synthesized in excellent yield and on a large scale.
关键词 Palladium-catalyst coupling reaction preparation BIARYL polyaryl.
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Synthesis of biaryls using palladium nanoparticles immobilized on peptide nanofibers as catalyst and hydroxybenzotriazole as novel phenylating reagent
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作者 Arash Ghorbani-Choghamarani Zahra Taherinia 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2017年第3期469-474,共6页
Peptide nanofibers decorated with palladium nanoparticles catalyzed direct coupling of aryl halides with hydroxybenzotriazole to afford the corresponding biaryls in good to excellent yields.The coupling reactions proc... Peptide nanofibers decorated with palladium nanoparticles catalyzed direct coupling of aryl halides with hydroxybenzotriazole to afford the corresponding biaryls in good to excellent yields.The coupling reactions proceeded under simple,green,and mild conditions.The peptide nanofibers were used as recyclable supports in the coupling reactions.This approach is the first to use hydroxybenzotriazole as a phenylating agent. 展开更多
关键词 Peptide nanofiber Hydroxybenzotriazole BIARYL PEG Palladium
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A facile approach to asymmetrical biaryls via coupling reaction of aryl halides with sodium tetraphenylborate catalyzed by MCM-41-supported sulfur palladium(0) complex
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作者 Qiu Hua Xu Ping Ping Wang Ming Zhong Cai 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第4期387-389,共3页
Various functionalized asymmetrical biaryls can be synthesized in high to excellent yields via coupling reaction of aryl iodides or bromides with NaBPh4 catalyzed by MCM-41-supported sulfur palladium(0) complex. Thi... Various functionalized asymmetrical biaryls can be synthesized in high to excellent yields via coupling reaction of aryl iodides or bromides with NaBPh4 catalyzed by MCM-41-supported sulfur palladium(0) complex. This palladium complex can be easily recovered and reused many times without loss of activity. 展开更多
关键词 Asymmetrical biaryl NaBPh4 Aryl halide PALLADIUM Coupling reaction
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An unprecedented synthesis of axially chiral biaryls by rearrangement and aromatization of carbocations with central-to-axial conversion of chirality
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作者 Qi Liu Xue-Dong Li +1 位作者 Liang Cheng Li Liu 《Science China Chemistry》 SCIE EI CAS CSCD 2024年第9期2998-3003,共6页
The central-to-axial chirality conversion represents a fascinating class of chemical processes consisting of the destruction of stereogenic centers and the simultaneous installation of axial chiral elements,which prov... The central-to-axial chirality conversion represents a fascinating class of chemical processes consisting of the destruction of stereogenic centers and the simultaneous installation of axial chiral elements,which provides efficient methods for the preparation of axially chiral compounds.However,developing catalytic asymmetric approaches for constructing these central chirality precursors and the efficient central-to-axial chirality conversion remains a challenge due to the requirement of aromatization or elimination process.In this work,we have developed an unprecedented enantioselective intramolecular FriedelCrafts alkylation with unactivated-ketone carbonyls from which a chiral tertiary alcohol was generated with high efficiency and excellent enantioselectivity.In addition,the central-to-axial chirality conversion strategy has been successfully applied to the synthesis of enantioenriched biaryls via a less-explored carbocation-initiated rearrangement and aromatization under the promotion of Lewis acid.This methodology provided a straightforward and sustainable access to a broad range of biaryl-2-carboxylic acid and in excellent yields(up to 92%)and excellent central-to-axial chirality conversion(up to 99%conversion percentage).This work could be a great model for developing new methods for synthesizing axially chiral biaryls and a general protocol for the rearrangement and aromatization of carbocations for further functionalization. 展开更多
关键词 br?nsted acid catalysis desymmetrization phosphoric acid axially chiral biaryls central-to-axial conversion
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Carbene-Catalyzed Asymmetric Ring-Opening Reaction of Biaryl Lactams to Access Axially Chiral Biaryls
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作者 Guanjie Wang Guowei Yuan +6 位作者 Chenlong Wei Ye Zhang Haibin Zhu Weiqi Yang Dongping Shi Xiaoxiang Zhang Zhenqian Fu 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第15期1734-1740,共7页
Axially chiral biaryls represent the most important class of atropisomers,and they widely exist in natural products and biologically active molecules.They also constitute a unique scaffold for chiral ligands and catal... Axially chiral biaryls represent the most important class of atropisomers,and they widely exist in natural products and biologically active molecules.They also constitute a unique scaffold for chiral ligands and catalysts in organic synthesis.The development of synthetic methods to obtain such chiral compounds has received widespread attention,among which catalytically atroposelective ring-opening of configurationally labile compounds represents one of the most attractive strategies.Various substrates with strained cyclic structures,such as the renowned Bringmann's lactones,can undergo asymmetric transformation into stable atropisomers.Known advancement primarily relies on metal catalyst combined with well-designed chiral ligands,the approaches utilizing organocatalysis as a critical resolution strategy are notably scarce.In this study,we disclosed a N-heterocyclic carbene(NHC)-catalyzed asymmetric ring-opening reaction of biaryl lactams via direct atroposelective nucleophilic activation.The optimized bulky carbene catalyst ensures that the reaction can proceed under mild conditions,affording the desired product with good to excellent yields and atroposelectivity. 展开更多
关键词 N-Heterocyclic carbene Axially chiral biaryls Organocatalysis Ring-opening reactions Dibenzo cyclic lactams Axially chiral amino acids Amide C-N bond activation ATROPISOMERISM Asymmetric catalysis LACTAMS
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Theoretical insights into the [4+2]/retro [4+2] cycloaddition approach to the synthesis of biaryls and polycyclic aromatics
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作者 LI XinYao XU JiaXi 《Science China Chemistry》 SCIE EI CAS 2013年第5期633-640,共8页
A domino [4+2]/retro [4+2] cycloaddition process of cyclohexadienes with arylethynes or benzyne providing access to biaryls and polycyclic aromatics has been studied theoretically using density functional theory calcu... A domino [4+2]/retro [4+2] cycloaddition process of cyclohexadienes with arylethynes or benzyne providing access to biaryls and polycyclic aromatics has been studied theoretically using density functional theory calculations. It has been found that the initial Diels-Alder (D-A) reaction acts as the rate-determining step and the consequent [4+2] cycloreversion reaction is feasible under the conditions used. Furthermore, the D-A reaction affects the regioselectivity, the origin of which is essentially derived from the good match of orbital coefficients between dienes and dienophiles as shown by using frontier molecular orbital (FMO) theory. Further investigation of the reactivity reveals that the reactions are predicted to fail to occur if an electron-donor group in the diene or an electron-acceptor group in the dienophile is lacking, as a consequence of the increased FMO energy gap. By further exploring the scope of substrates computationally, benzyne as an active dienophile was predicted to react with a variety of dienes in a cascade reaction under mild conditions with a low energy barrier, with the rate-determining step being the retro [4+2] cycloaddition. 展开更多
关键词 [4+2]/retro [4+2] cycloaddition biaryls polycyclic aromatics regioselectivity DFT study
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Merging C–H and C–C Activation in Pd(Ⅱ)-Catalyzed Enantioselective Synthesis of Axially Chiral Biaryls
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作者 Hao-Ming Chen Gang Liao +3 位作者 Cheng-Kai Xu Qi-Jun Yao Shuo Zhang Bing-Feng Shi 《CCS Chemistry》 CAS 2021年第12期455-465,共11页
The merging of C-H and C-C bond cleavage into one single chemical process remains a daunting challenge,especially in an asymmetric manner.Herein,a Pd(Ⅱ)-catalyzed enantioselective tandem C-H/C-C activation for the sy... The merging of C-H and C-C bond cleavage into one single chemical process remains a daunting challenge,especially in an asymmetric manner.Herein,a Pd(Ⅱ)-catalyzed enantioselective tandem C-H/C-C activation for the synthesis of axially chiral biaryls is described.Two types of simple cyclopropanes,such as vinylcyclopropanes and cyclopropanols,were used as efficient and readily available coupling partners. 展开更多
关键词 palladium C–H activation C–C cleavage atroposelectivity axially chiral biaryls
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Ni-Catalyzed Cross Coupling ofAryl Grignard Reagents with Aryl Halides in a Nonpolar Solvent and an Efficient Synthesis of Biaryls Under Neat Conditions 被引量:1
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作者 WU Qiang JIN Rizhe +7 位作者 KANG Chuanqing CHEN Wenhui BIAN Zheng MA Xiaoye DING Jinying GUO Haiquan QIU Xuepeng GAO Llanxun 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2016年第1期55-61,共7页
This study details Ni-catalyzed cross coupling of aryl Grignard reagents with aryl halides in toluene, a nonpolar solvent with a high boiling point. The reaction was applied for the synthesis of various biaryls in goo... This study details Ni-catalyzed cross coupling of aryl Grignard reagents with aryl halides in toluene, a nonpolar solvent with a high boiling point. The reaction was applied for the synthesis of various biaryls in good yields without the introduction of a large steric ligand. The Kumada-Tamao-Corriu(KTC) reaction in toluene was then successfully modified to proceed under neat conditions for the efficient syntheses of symmetrical biaryls, particularly in large-scale preparations. Unactivated aryl chlorides show higher reactivity than aryl bromides, particularly under neat conditions. Mechanistic investigations suggest a radical procedure for the catalytic cycle, and the origin of the radical intermediates being aryl halides. 展开更多
关键词 CROSS-COUPLING Nickel BIARYL Reaction mechanism Neat condition
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Preparation of polymer-supported phosphine from ferrocene for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions 被引量:2
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作者 Hong Wei Yu Qing Song Tong +3 位作者 Yi Ru Peng Li Jia Ji Cheng Shi Zi Lin Jin 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第1期37-40,共4页
Polymer-supported phosphine ligand 3b derived from ferrocene was prepared, and applied in palladium-catalyzed Suzuki- Miyaura reactions. A range of aryl bromides can couple with phenylboronic acid to obtain correspond... Polymer-supported phosphine ligand 3b derived from ferrocene was prepared, and applied in palladium-catalyzed Suzuki- Miyaura reactions. A range of aryl bromides can couple with phenylboronic acid to obtain corresponding biaryls in excellent yields. The recycling of the polymer-bound catalyst was tested without adding palladium. 展开更多
关键词 IMMOBILIZATION Palladium Suzulki-Miyaura reaction BIARYL Catalysis
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Alkoxy substituted MeO-BIPHEP-type diphosphines ligands for asymmetric hydrogenation of aryl ketones 被引量:2
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作者 Meng Lin Ma Zong Hai Peng +3 位作者 Yu Guo Li Chen Hua Chen Xian Jun Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第5期576-579,共4页
In this paper,a series of optically active MeO-BIPHEP-type ligands,(S)-6,6′-dimethoxy-2,2’-bis(di-p-alkoxyphenylphosphine)- 1,1′-biphenyl were synthesized and used to prepare the ruthenium complex.The effects o... In this paper,a series of optically active MeO-BIPHEP-type ligands,(S)-6,6′-dimethoxy-2,2’-bis(di-p-alkoxyphenylphosphine)- 1,1′-biphenyl were synthesized and used to prepare the ruthenium complex.The effects of para-substituted were observed,the results showed that the ruthenium catalysts[diphosphine RuCl;diamine]containing both t-Bu and i-Pr substitutions have better activities and enantioselectivities than the non-substituted ruthenium catalysts in the asymmetric hydrogenation of acetophenone. 展开更多
关键词 Aryl ketone Asymmetric hydrogenation Biaryl phosphines ligands Ruthenium complex
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Suzuki Coupling Reaction Catalyzed by Cyclopalladated Complexes of Tertiary Arylamines in Ionic Liquid 被引量:1
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作者 Hua YI Jin Biao LIU +1 位作者 Qiang LI Jie TANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第9期1173-1176,共4页
Suzuki cross-coupling reaction of phenylboronic acid with aryl halides catalyzed by cyclopalladated complexes of tertiary arylamines immobilized in ionic liquid [Bmim]^+BF4^- was reported. The catalytic system proved... Suzuki cross-coupling reaction of phenylboronic acid with aryl halides catalyzed by cyclopalladated complexes of tertiary arylamines immobilized in ionic liquid [Bmim]^+BF4^- was reported. The catalytic system proved to be efficient and be reused at least 3 times without significant loss of activity. 展开更多
关键词 Cyclopalladated complex aryl halides Suzuki coupling BIARYL ionic liquid
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Microwave-promoted Palladium Catalyzed Suzuki Cross-coupling Reaction in Water 被引量:1
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作者 LinBAI JinXianWANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第3期286-287,共2页
A simple, rapid and environmental friendly method for the synthesis of biaryl compounds under microwave irradiation is reported.
关键词 Suzuki coupling palladium catalyst biaryl compounds microwave irradiation.
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Synthesis of 3-Biaryl-1-ferrocenyl-2-propene-1-ones
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作者 QingBaoSONG ShangDongYANG +3 位作者 TianHuaSHEN YongQiangWANG YongXiangMA XiaoLiWU 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第6期569-571,共3页
The novel structures of organometallic compounds 3-biaryl-1-ferrocenyl-2-propene- 1-ones 5 were synthesized for nonlinear optical chromophores by Suzuki cross-coupling reaction. Their structures were determined with ... The novel structures of organometallic compounds 3-biaryl-1-ferrocenyl-2-propene- 1-ones 5 were synthesized for nonlinear optical chromophores by Suzuki cross-coupling reaction. Their structures were determined with elemental analyses, 1H NMR spectra and 13C NMR spectra. 展开更多
关键词 NLO materials palladium catalyst cross-coupling reaction FERROCENE biaryl.
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Palladium Catalyzed Synthesis of Fluorine-containing 3-Biaryl-1-ferrocenyl-2-propene-1-one
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作者 QingBaoSONG RuXiangLIN TianHuaSHEN 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第1期35-37,共3页
The novel organometallic compounds, 3-[4'(or 2')-(4''-fluorophenyl)] phenyl-1-ferroc- enyl-2-propen-1-ones 5 were synthesized for nonlinear optical chromophores by Pd (0) catalyzed Suzuki cross-coupl... The novel organometallic compounds, 3-[4'(or 2')-(4''-fluorophenyl)] phenyl-1-ferroc- enyl-2-propen-1-ones 5 were synthesized for nonlinear optical chromophores by Pd (0) catalyzed Suzuki cross-coupling reaction. Their structures were established with elemental analysis, MS, IR and H NMR spectroscopies. 1 展开更多
关键词 NLO materials palladium catalyst cross-coupling reaction BIARYL ferrocene.
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Nation-Teflon bimembrane-supported palladium catalysts for Suzuki coupling reactions
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作者 Li Ting Chai Yang Zhou Li Wei Wei Wang Quan Rui Wang Feng Gang Tao 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第12期1460-1462,共3页
Nation-Teflon bimembrane was used as an efficient support for the preparation and application of heterogeneous palladium catalysts. The supported palladium catalysts exhibit high activity and stability in the Suzuki c... Nation-Teflon bimembrane was used as an efficient support for the preparation and application of heterogeneous palladium catalysts. The supported palladium catalysts exhibit high activity and stability in the Suzuki cross-coupling of aryl bromides with arylboronic acids to afford the corresponding biaryls in good to excellent yields, and can be readily recovered and reused several times without significant loss of activity. 展开更多
关键词 Nation-Teflon bimembrane-supported Palladium catalysts Suzuki reaction BIARYL
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Photocatalytic Site-Selective Cascade Radical Addition of Biaryl Ynones for the Construction of Spiro-and Fused Carbon Rings
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作者 Kairui Liu Chunhang Zhao +5 位作者 Liji Gu Xiang Li Jiali Yan Siqi Lao Weiwei Huan Yan Zhang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第14期1599-1605,共7页
Functionalized free radical addition/cyclization reactions represent an efficient way for introducing new functionality or coupling fragments to molecules.Ynones are good regional selectivity radical acceptors in orga... Functionalized free radical addition/cyclization reactions represent an efficient way for introducing new functionality or coupling fragments to molecules.Ynones are good regional selectivity radical acceptors in organic synthesis,and many of bio-relevant cyclic compounds could be easily obtained by direct radical cyclization reaction.Here,we report a photocatalytic cascade radical addition of biaryl ynones,for the divergent synthesis of privileged carbon cycles.Additionally,further transformation of the multi-functional group product into a variety of other derivatives demonstrates the synthetic value of this developed method. 展开更多
关键词 YNONES Photocatalysis Cascade cyclization Alkoxycarbonyl radical DEAROMATIZATION biaryls Regioselectivity Radical reactions
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Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Axially Chiral Compounds 被引量:10
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作者 Bing-Chao Da Shao-Hua Xiang +1 位作者 Shaoyu Li Bin Tan 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第7期1787-1796,共10页
The well-defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules,advanced materials,organocatalysts as well as chiral ligands in asymmetric tran... The well-defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules,advanced materials,organocatalysts as well as chiral ligands in asymmetric transformations.The demonstrated usefulness and untapped potential of axially chiral structural motifs stimulate increasing efforts to develop novel and efficient approaches for their preparation.In this regard,the chiral phosphoric acids broadly used in asymmetric Brønsted acid catalysis have shown high relevance for atroposelective synthesis as well.Our strong interest in reaction chemistry of atropisomers has established a rewarding research programme in our group.The course of studies will be recounted in this account,with discussion focused on the use of chiral phosphoric acids to catalyze construction of several key axially chiral structures such as BINAM,BINOL,NOBIN,arylquinones,SPINOL,arylpyrrole analogues and axially chiral alkenes. 展开更多
关键词 Axial chirality ORGANOCATALYSIS Chiral phosphoric acid biaryls Asymmetric synthesis
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Catalytic Atroposelective Catellani Reaction Enables Construction of Axially Chiral Biaryl Monophosphine Oxides 被引量:2
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作者 Qiang Feng Xingxing Ma +3 位作者 Wen Bao Shi-Jun Li Yu Lan Qiuling Song 《CCS Chemistry》 CAS 2021年第12期377-387,共11页
An unprecedented atroposelective Catellani reaction between phosphine oxide-containing aryl bromides,aryliodides,and nucleophiles for the construction of phosphine-containing biaryl atropisomers was established using ... An unprecedented atroposelective Catellani reaction between phosphine oxide-containing aryl bromides,aryliodides,and nucleophiles for the construction of phosphine-containing biaryl atropisomers was established using an enantiopure norbornene derivative as the chiral mediator.A broad range of atropisomeric biaryl-based monophosphine oxides were obtained in good efficiency with excellent enantioselectivity. 展开更多
关键词 axial chirality biaryls Catellani reaction atroposelectivity biaryl monophosphine oxides
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Catalytic asymmetric Catellani-type reaction: A powerful tool for axial chirality construction 被引量:3
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作者 Yue Dong Renshuai Liu Wei Wang 《Green Synthesis and Catalysis》 2020年第2期83-85,共3页
This highlight summarizes a recent development of a catalytic enantioselective Catellani-type reaction for the synthesis of axially chiral biaryls.The chirality induction is solely governed by chiral norbornene ligand... This highlight summarizes a recent development of a catalytic enantioselective Catellani-type reaction for the synthesis of axially chiral biaryls.The chirality induction is solely governed by chiral norbornene ligand in the Pd mediated ortho C–H functionalization and ipso cross-coupling transformation.The preparative power of the methodology is demonstrated as a powerful manifold for the divergent synthesis of structurally diverse axially chiral biaryls and chiral fluorenols. 展开更多
关键词 Axially chiral biaryls Asymmetric Catellani reaction C-H functionalization Cross coupling Divergent synthesis
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