A simple and additive-free protocol has been developed for the preparation ofβ-keto phosphorodithioates through the three-component reaction of easily available sulfoxonium ylides,P_(4)S_(10),and alcohols.The present...A simple and additive-free protocol has been developed for the preparation ofβ-keto phosphorodithioates through the three-component reaction of easily available sulfoxonium ylides,P_(4)S_(10),and alcohols.The present geminal hydro-phosphorodithiolation reaction was performed at room temperature to construct a series ofβ-keto phosphorodithioates in the absence of any metal reagents,bases,or additives.展开更多
A thermally-induced multi-component reaction of CF_(3)-substituted imidoyl sulfoxonium ylides(TFISYs),amines and(triphenylphosphonio)difluoroacetate(PDFA)has been developed,allowing a facile access to 2-trifluoromethy...A thermally-induced multi-component reaction of CF_(3)-substituted imidoyl sulfoxonium ylides(TFISYs),amines and(triphenylphosphonio)difluoroacetate(PDFA)has been developed,allowing a facile access to 2-trifluoromethyl-4-aminoquinolines in high yields.The reaction proceeds smoothly with or without the addition of sulfur and utilizes difluorocarbene as a C1 synthon under simply heating conditions.Mechanistic study reveals that in-situ generated thiocarbonyl fluoride,isothiocyanate or gem-difluoroalkene might act as the key reaction intermediates.展开更多
Rhodium(Ⅲ)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of C -H alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides....Rhodium(Ⅲ)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of C -H alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides. Notably, this transformation could smoothly proceed with high yields, good regioselectivity, and feature broad group tolerance and under redox-neutral condition to avoid external oxidant. The titled products are potentially important building blocks in the organic synthesis through various chemical transformations.展开更多
Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(Ⅱ) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselec...Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(Ⅱ) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity,providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.展开更多
Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-...Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives.The synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.展开更多
A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(Ⅲ)-catalyzed C-H activation and[3+3]annulation between sulfoxonium ylides and dioxazolones.The reaction is conducted under base-free condi...A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(Ⅲ)-catalyzed C-H activation and[3+3]annulation between sulfoxonium ylides and dioxazolones.The reaction is conducted under base-free conditions and tolerates various functional groups.Starting from diverse readily available sulfoxonium ylides and dioxazolones,a variety of benzoxazinones could be synthesized in one step in 32%-75%yields.展开更多
A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported.The reaction occurred under sole visible light irradiation...A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported.The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives,affording the corresponding sulfoxonium ylides in moderate to good yields.The success of late-stage modification of natural isolates or drug candidates,scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.展开更多
An efficient and practical synthetic approach was developed for the tandem synthesis of trisubstituted 2-pyrone derivatives from sulfoxonium ylides and cyclopropenones.This[3+3]annulation reaction was carried out unde...An efficient and practical synthetic approach was developed for the tandem synthesis of trisubstituted 2-pyrone derivatives from sulfoxonium ylides and cyclopropenones.This[3+3]annulation reaction was carried out under transition-metal-free conditions.A broad range of functional groups were tolerant under mild conditions,and a variety of 2-pyrones were obtained in moderate to good yields.展开更多
Doyle-Kirmse rearrangement reactions have received continuous attention as an important method for constructing complex chemical structures. Herein, we disclosed an efficient rhodium-catalyzed DoyleKirmse rearrangemen...Doyle-Kirmse rearrangement reactions have received continuous attention as an important method for constructing complex chemical structures. Herein, we disclosed an efficient rhodium-catalyzed DoyleKirmse rearrangement reaction, which can simultaneously construct C–C bonds and C–X(X = S/Se) bonds using sulfoxonium ylides as starting materials to obtain sulfur-or selenium-containing compounds. This strategy is characterized by the safer and greener carbene precursor, high yields and broad substrate scope, possessing a wide range of application.展开更多
基金supported by the Natural Science Foundation of Shandong Province(No.ZR2021MB065)Scientific Research Startup Foundation of Qufu Normal University and National Natural Science Foundation of China(No.22101237)。
文摘A simple and additive-free protocol has been developed for the preparation ofβ-keto phosphorodithioates through the three-component reaction of easily available sulfoxonium ylides,P_(4)S_(10),and alcohols.The present geminal hydro-phosphorodithiolation reaction was performed at room temperature to construct a series ofβ-keto phosphorodithioates in the absence of any metal reagents,bases,or additives.
基金financial support from K.C.Wong Education Foundation(GJTD-2020-08).
文摘A thermally-induced multi-component reaction of CF_(3)-substituted imidoyl sulfoxonium ylides(TFISYs),amines and(triphenylphosphonio)difluoroacetate(PDFA)has been developed,allowing a facile access to 2-trifluoromethyl-4-aminoquinolines in high yields.The reaction proceeds smoothly with or without the addition of sulfur and utilizes difluorocarbene as a C1 synthon under simply heating conditions.Mechanistic study reveals that in-situ generated thiocarbonyl fluoride,isothiocyanate or gem-difluoroalkene might act as the key reaction intermediates.
基金partial financial support from the Ministry of Science and Technology of China (No. 2016YFE0132600)Zhengzhou University
文摘Rhodium(Ⅲ)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of C -H alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides. Notably, this transformation could smoothly proceed with high yields, good regioselectivity, and feature broad group tolerance and under redox-neutral condition to avoid external oxidant. The titled products are potentially important building blocks in the organic synthesis through various chemical transformations.
基金support from the National Natural Science Foundation of China (Nos.81373259 and 81573286)Sichuan Science and Technology Program (Nos.2020YJ0221 and 2018JY0537)。
文摘Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(Ⅱ) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity,providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.
基金the National Natural Science Foundation of China(No.21702106)the Natural Science Foundation of Jiangsu Province(No.BK20170967)the Start-up Grant from Nanjing Tech University(No.39839101)for financial support。
文摘Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives.The synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.
基金financial support from the Hunan Provincial Innovation Foundation for Postgraduate(No.CX20190267)Natural Science Foundation of Hunan Province(No.2020JJ4171)。
文摘A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(Ⅲ)-catalyzed C-H activation and[3+3]annulation between sulfoxonium ylides and dioxazolones.The reaction is conducted under base-free conditions and tolerates various functional groups.Starting from diverse readily available sulfoxonium ylides and dioxazolones,a variety of benzoxazinones could be synthesized in one step in 32%-75%yields.
基金the National Natural Science Foundation of China(Nos.21971001 and 21702001)the Natural Science Foundation of Anhui Province(No.1808085MB47)the Open Fund for Discipline Construction,Institute of Physical Science and Information Technology,Anhui University,and the Start-Up Grant from Anhui University for financial support of this work.
文摘A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported.The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives,affording the corresponding sulfoxonium ylides in moderate to good yields.The success of late-stage modification of natural isolates or drug candidates,scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.
基金This work was supported by the National Natural Science Foundation of China(Nos.81573286 and 81373259).
文摘An efficient and practical synthetic approach was developed for the tandem synthesis of trisubstituted 2-pyrone derivatives from sulfoxonium ylides and cyclopropenones.This[3+3]annulation reaction was carried out under transition-metal-free conditions.A broad range of functional groups were tolerant under mild conditions,and a variety of 2-pyrones were obtained in moderate to good yields.
基金supported by Sichuan Science and Technology Program (No.2020YJ0221)。
文摘Doyle-Kirmse rearrangement reactions have received continuous attention as an important method for constructing complex chemical structures. Herein, we disclosed an efficient rhodium-catalyzed DoyleKirmse rearrangement reaction, which can simultaneously construct C–C bonds and C–X(X = S/Se) bonds using sulfoxonium ylides as starting materials to obtain sulfur-or selenium-containing compounds. This strategy is characterized by the safer and greener carbene precursor, high yields and broad substrate scope, possessing a wide range of application.
