An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-fre...An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-free conditions has been developed.The mild reaction conditions,high reaction efficiency,operational simplicity,short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds.展开更多
Herein we summarized some clean preparation examples to emphasize the concept of dual roles design(or named as "two birds one stone strategy") in green and sustainable chemistry.In those examples,the reactan...Herein we summarized some clean preparation examples to emphasize the concept of dual roles design(or named as "two birds one stone strategy") in green and sustainable chemistry.In those examples,the reactants and/or solvent play dual roles rendering a cleaner organic preparation process.Consequently,both the chemical waste and manufacturing cost could be reduced.展开更多
We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water.This ligand-free Suzuki reaction is performed in th...We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water.This ligand-free Suzuki reaction is performed in the presence of diisopropylamine and gives 2-or 3-arylated pyridyl N-oxide derivatives in good to excellent yields within 1 h.展开更多
A highly enantioselective Michael addition of nitro esters to 2-enoyl-pyridine N-oxides was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields and with up to 96% e...A highly enantioselective Michael addition of nitro esters to 2-enoyl-pyridine N-oxides was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields and with up to 96% ee. Moreover, asymmetric Michael addition product of nitromethane to 2-enoyl-pyridine N-oxides can be obtained in one step. An analogue of nicotine, dihydro-2H-pyrrol 4b was synthesized with this developed method.展开更多
Aliphatic amine N-oxides, particularly （CH<sub>3</sub>）<sub>3</sub>NO, have been widely used as O-atom transfer reagents in organometallic chemistry. Recently the systematic kinetic studies o...Aliphatic amine N-oxides, particularly （CH<sub>3</sub>）<sub>3</sub>NO, have been widely used as O-atom transfer reagents in organometallic chemistry. Recently the systematic kinetic studies on O-atom transfer reactions have been reported in detail. However, little is known about the use of pyridine N-oxides and the related aromatic amine N-oxides as O-atom transfer reagents in organometallic chemistry, and no kinetic or展开更多
Straight-chain aliphatic tert-amine N-oxides were found to be useful oxidizing agent for epoxidation of tri- and tetra-substituted perfluoroalkenes under mild conditions in high yields. The process for epoxidation by ...Straight-chain aliphatic tert-amine N-oxides were found to be useful oxidizing agent for epoxidation of tri- and tetra-substituted perfluoroalkenes under mild conditions in high yields. The process for epoxidation by employing tri-n-butylamine N-oxide gave the best result in the reagent survey.展开更多
A new preparation method of the N-ethyl 7,17-seco C_(19)-diterpenoid alkaloids(5)and(6)by pyrolysis of the N-oxides(3)and(4),respectively, in anhydrous diglyme is described.A probable reaction mechanism for the pyroly...A new preparation method of the N-ethyl 7,17-seco C_(19)-diterpenoid alkaloids(5)and(6)by pyrolysis of the N-oxides(3)and(4),respectively, in anhydrous diglyme is described.A probable reaction mechanism for the pyroly- sis is presented and studied preliminarily.展开更多
A highly efficient enantioselective construction of heterobiaryl N-oxides was developed.A series of axially chiral heterobiaryl N-oxides were generated via the cascade reaction of aminobenzamides with heterobiaryl ald...A highly efficient enantioselective construction of heterobiaryl N-oxides was developed.A series of axially chiral heterobiaryl N-oxides were generated via the cascade reaction of aminobenzamides with heterobiaryl aldehydes in the presence of chiral phosphoric acids.A number of atropisomers were afforded in moderate to good yields with excellent enantioselectivities and diastereoselectivities.Preliminary results demonstrate that the heterobiaryl N-oxides can be utilized as efficient chiral ligands in asymmetric catalysis.展开更多
A simple and efficient method for the synthesis of 2-sulfonylquinoline from deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acid induced by visible light is presented.This protocol shows a broad sub...A simple and efficient method for the synthesis of 2-sulfonylquinoline from deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acid induced by visible light is presented.This protocol shows a broad substrate scope,and desired products with various substituents can be formed in moderate to high yields at room temperature.展开更多
Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect r...Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect regioselectivity,a broad substrate scope,and isolated yields of up to 92%.We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.展开更多
基金financial support from the Hunan Provincial Natural Science Foundation of China (No.2019JJ20008)
文摘An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-free conditions has been developed.The mild reaction conditions,high reaction efficiency,operational simplicity,short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds.
基金financial support from the National Natural Science Foundation of China(Nos.21545010 and 31527803)Hunan Provincial Natural Science Foundation of China(No. 2019JJ20008)
文摘Herein we summarized some clean preparation examples to emphasize the concept of dual roles design(or named as "two birds one stone strategy") in green and sustainable chemistry.In those examples,the reactants and/or solvent play dual roles rendering a cleaner organic preparation process.Consequently,both the chemical waste and manufacturing cost could be reduced.
基金financial support from the National Natural Science Foundation of China(No.21276043)
文摘We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water.This ligand-free Suzuki reaction is performed in the presence of diisopropylamine and gives 2-or 3-arylated pyridyl N-oxide derivatives in good to excellent yields within 1 h.
基金financial support from the National Nature Science Foundation of China(Nos. 21432009, 21672200, 21472177,21772185)the assistance of the product characterization from the Chemistry Experiment Teaching Center of University of Science and Technology of Chinasupported by the Strategic Priority Research Program of the Chinese Academy of Sciences(No. XDB20000000)
文摘A highly enantioselective Michael addition of nitro esters to 2-enoyl-pyridine N-oxides was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields and with up to 96% ee. Moreover, asymmetric Michael addition product of nitromethane to 2-enoyl-pyridine N-oxides can be obtained in one step. An analogue of nicotine, dihydro-2H-pyrrol 4b was synthesized with this developed method.
基金Project supported by the National Natural Science Foundation of China
文摘Aliphatic amine N-oxides, particularly （CH<sub>3</sub>）<sub>3</sub>NO, have been widely used as O-atom transfer reagents in organometallic chemistry. Recently the systematic kinetic studies on O-atom transfer reactions have been reported in detail. However, little is known about the use of pyridine N-oxides and the related aromatic amine N-oxides as O-atom transfer reagents in organometallic chemistry, and no kinetic or
文摘Straight-chain aliphatic tert-amine N-oxides were found to be useful oxidizing agent for epoxidation of tri- and tetra-substituted perfluoroalkenes under mild conditions in high yields. The process for epoxidation by employing tri-n-butylamine N-oxide gave the best result in the reagent survey.
文摘A new preparation method of the N-ethyl 7,17-seco C_(19)-diterpenoid alkaloids(5)and(6)by pyrolysis of the N-oxides(3)and(4),respectively, in anhydrous diglyme is described.A probable reaction mechanism for the pyroly- sis is presented and studied preliminarily.
基金supported by the National Natural Science Foundation of China(21871160,21672121,22071130)the fellowship of Tsinghua-Peking Centre for Life Sciences(CLS).
文摘A highly efficient enantioselective construction of heterobiaryl N-oxides was developed.A series of axially chiral heterobiaryl N-oxides were generated via the cascade reaction of aminobenzamides with heterobiaryl aldehydes in the presence of chiral phosphoric acids.A number of atropisomers were afforded in moderate to good yields with excellent enantioselectivities and diastereoselectivities.Preliminary results demonstrate that the heterobiaryl N-oxides can be utilized as efficient chiral ligands in asymmetric catalysis.
基金supported by the National Natural Science Foundation of China (21402103, 21772107)the China Postdoctoral Science Foundation (150030)+1 种基金the Research Fund of Qingdao Agricultural University’s Highlevel Person (631303)Shandong province key research and development plan(GG201809130228)~~
文摘A simple and efficient method for the synthesis of 2-sulfonylquinoline from deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acid induced by visible light is presented.This protocol shows a broad substrate scope,and desired products with various substituents can be formed in moderate to high yields at room temperature.
基金the National Natural Science Foundation of China(Nos.21977056,21732002,21672117,21602117,21772104,31760527)the Tianjin Natural Science Foundation(No.16JCZDJC32400)for generous financial support for our programs。
文摘Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect regioselectivity,a broad substrate scope,and isolated yields of up to 92%.We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.
