Reported herein is the first example of electrochemical selenocyanation of imidazo[1,5-a]quinolines with KSeCN under metal catalyst-and chemical oxidant-free conditions.This sustainable strategy shows a broad scope an...Reported herein is the first example of electrochemical selenocyanation of imidazo[1,5-a]quinolines with KSeCN under metal catalyst-and chemical oxidant-free conditions.This sustainable strategy shows a broad scope and great compatibility with functional groups,and affords synthetically and biologically important selenocyanated imidazo[1,5-a]quinolines in good to excellent yields with cheap graphite and Ni plates as the electrodes.The gram-scale synthesis was also successfully conducted,which might demonstrate the potential value of this electrochemical protocol.展开更多
Comprehensive Summary A novel transient SET mediator approach has been developed for the photoinduced radical-radical cross coupling reaction.Using the in-situ generated thianthrene radical cation as the transient SET...Comprehensive Summary A novel transient SET mediator approach has been developed for the photoinduced radical-radical cross coupling reaction.Using the in-situ generated thianthrene radical cation as the transient SET mediator,the thiocyanation and selenocyanation of aryl thianthrenium salts have been realized under the mild conditions without the need for photocatalyst or single electron donor.In comparison with the photocatalyst enabled process,the protocol features mild conditions,simple manipulation,a broad substrate scope,excellent functional group and heterocycle tolerance.Due to the feasible accessibility of aryl thianthrenium salts,this method has also been applied in the efficient synthesis of a bioactive molecule,and the late-stage functionalization of complex arenes.展开更多
Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap ...Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap biomass lactic acid as the reaction media and catalyst, a sustainable protocol for the synthesis of Z-3-selenocyanatoacrylates and analogues through green selenocyanation of activated alkynes has been achieved. A principal advantage of this protocol is that the usage of organic volatile compounds can be avoided entirely, as the conversion of substrate is almost quantitative or quantitative with a minimal amount of lactic acid employed as reaction media, and the pure products can be conveniently collected through water precipitation.展开更多
基金the National Natural Science Foundation of China(Nos.21602119,21702013)the Foundation of He’nan Educational Committee(No.16A150057)+2 种基金Program for Science and Technology Innovation Talents in Universities of Henan Province(No.19HASTIT033)the Beijing Natural Science Foundation(No.2184115)the Fundamental Research Funds for the Central Universities(Nos.XK1802-6,buctrc201721)。
文摘Reported herein is the first example of electrochemical selenocyanation of imidazo[1,5-a]quinolines with KSeCN under metal catalyst-and chemical oxidant-free conditions.This sustainable strategy shows a broad scope and great compatibility with functional groups,and affords synthetically and biologically important selenocyanated imidazo[1,5-a]quinolines in good to excellent yields with cheap graphite and Ni plates as the electrodes.The gram-scale synthesis was also successfully conducted,which might demonstrate the potential value of this electrochemical protocol.
基金We gratefully acknowledge National Natural Science Foundation of China(22101291,22171277,21821002)National Key R&D Program of China(2021YFA1500200)+1 种基金Shanghai Rising-Star Program(20QA1411400)Shanghai Institute of Organic Chemistry,and State Key Laboratory of Organometallic Chemistry for finan cial support.
文摘Comprehensive Summary A novel transient SET mediator approach has been developed for the photoinduced radical-radical cross coupling reaction.Using the in-situ generated thianthrene radical cation as the transient SET mediator,the thiocyanation and selenocyanation of aryl thianthrenium salts have been realized under the mild conditions without the need for photocatalyst or single electron donor.In comparison with the photocatalyst enabled process,the protocol features mild conditions,simple manipulation,a broad substrate scope,excellent functional group and heterocycle tolerance.Due to the feasible accessibility of aryl thianthrenium salts,this method has also been applied in the efficient synthesis of a bioactive molecule,and the late-stage functionalization of complex arenes.
基金financial support from the Natural Science Foundation of Hunan Provincial (Nos. 2019JJ50193 and 2019JJ20008)
文摘Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap biomass lactic acid as the reaction media and catalyst, a sustainable protocol for the synthesis of Z-3-selenocyanatoacrylates and analogues through green selenocyanation of activated alkynes has been achieved. A principal advantage of this protocol is that the usage of organic volatile compounds can be avoided entirely, as the conversion of substrate is almost quantitative or quantitative with a minimal amount of lactic acid employed as reaction media, and the pure products can be conveniently collected through water precipitation.
