An eco-friendly and convenient method is developed herein for the synthesis of S-aryl dithiocarbamates via visible-light-induced SET process of an EDA complex between thianthrenium salt functionalized arenes and dithi...An eco-friendly and convenient method is developed herein for the synthesis of S-aryl dithiocarbamates via visible-light-induced SET process of an EDA complex between thianthrenium salt functionalized arenes and dithiocarbamate anions under mild aqueous micellar conditions.This strategy indirectly realizes the method for constructing S-aryl dithiocarbamates through site-selective C−H functionalization of arenes.Most importantly,the reaction proceeded smoothly without addition of any photocatalyst,and the by-product thianthrene is recycled in quantity,ultimately minimizing the production of chemical waste.This protocol provides a promising synthesis candidate for the construction of valuable S-aryl dithiocarbamates,which also opens up a new avenue for micellar photocatalysis.展开更多
A novel and eco-friendly electrochemical activation of trifluoromethyl thianthrenium triflate(TT-CF_(3)^(+)OTf^(-))for trifluoromethylation of imidazole-fused heteroaromatic compounds was established.This method invol...A novel and eco-friendly electrochemical activation of trifluoromethyl thianthrenium triflate(TT-CF_(3)^(+)OTf^(-))for trifluoromethylation of imidazole-fused heteroaromatic compounds was established.This method involves the direct electrolysis of TT-CF_(3)^(+)OTf^(-)without the requirement of external oxidants or catalysts,aligning with the principles of green chemistry.A wide range of imidazole-fused heteroaromatic compounds including imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles have been successfully trifluoromethylated using this technique,exhibiting excellent compatibility with various functional groups and a broad substrate scope.Moreover,the method's applicability for one-pot sequential reactions enables the reduction of waste and resource consumption by eliminating the need for intermediate purification steps.展开更多
Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfo...Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfonohydrazides in moderate to good yields.This multicomponent reaction of trifluoromethyl thianthrenium triflate,alkynes,sulfur dioxide and hydrazines proceeds efficiently under visible light irradiation in the presence of photocatalyst at room temperature with broad substrate scope and excellent functional group compatibility.This reaction is highly stereoselective,and only(E)-isomers are obtained.Additionally,these trifluoromethyl-substituted vinyl sulfonohydrazides are further evaluated for anti-bacteria activity.In vitro activities of these compounds against Staphylococcus aureus(G+)and Escherichia coli(G-)are examined.展开更多
基金supported by the National Natural Science Foundation of China(No.22271170)the Scientific Research Foundation of Qingdao University of Science and Technology。
文摘An eco-friendly and convenient method is developed herein for the synthesis of S-aryl dithiocarbamates via visible-light-induced SET process of an EDA complex between thianthrenium salt functionalized arenes and dithiocarbamate anions under mild aqueous micellar conditions.This strategy indirectly realizes the method for constructing S-aryl dithiocarbamates through site-selective C−H functionalization of arenes.Most importantly,the reaction proceeded smoothly without addition of any photocatalyst,and the by-product thianthrene is recycled in quantity,ultimately minimizing the production of chemical waste.This protocol provides a promising synthesis candidate for the construction of valuable S-aryl dithiocarbamates,which also opens up a new avenue for micellar photocatalysis.
基金the financial support from the National Key R&D Program of China(2021YFB4001100,2021YFB4001101)the National Natural Science Foundation of China(21971224,22071222,and 22171249)+1 种基金the Natural Science Foundation of Henan Province(232300421363)the Science&Technology Innovation Talents in Universities of Henan Province(23HASTIT003).
文摘A novel and eco-friendly electrochemical activation of trifluoromethyl thianthrenium triflate(TT-CF_(3)^(+)OTf^(-))for trifluoromethylation of imidazole-fused heteroaromatic compounds was established.This method involves the direct electrolysis of TT-CF_(3)^(+)OTf^(-)without the requirement of external oxidants or catalysts,aligning with the principles of green chemistry.A wide range of imidazole-fused heteroaromatic compounds including imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles have been successfully trifluoromethylated using this technique,exhibiting excellent compatibility with various functional groups and a broad substrate scope.Moreover,the method's applicability for one-pot sequential reactions enables the reduction of waste and resource consumption by eliminating the need for intermediate purification steps.
基金Financial support from National Natural Science Foundation of China(No.21871053)the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang(No.2019R01005)the Open Research Fund of School of Chemistry and Chemical Engineering,Henan Normal University(2020ZD04)。
文摘Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfonohydrazides in moderate to good yields.This multicomponent reaction of trifluoromethyl thianthrenium triflate,alkynes,sulfur dioxide and hydrazines proceeds efficiently under visible light irradiation in the presence of photocatalyst at room temperature with broad substrate scope and excellent functional group compatibility.This reaction is highly stereoselective,and only(E)-isomers are obtained.Additionally,these trifluoromethyl-substituted vinyl sulfonohydrazides are further evaluated for anti-bacteria activity.In vitro activities of these compounds against Staphylococcus aureus(G+)and Escherichia coli(G-)are examined.
