Visible-light-induced organocatalyzed C(sp^(2))–H bond functionalization of 1,3-azoles with trifluoroacetylsilanes  

作　　者：Zhengyu Li Zeguo Zhang Zhihan Zhang Gang Zhou Yizhi Zhang Shanshan Liu Xiao Shen 

机构地区：[1]The Institute for Advanced Studies,Engineering Research Center of Organosilicon Compounds&Materials,Ministry of Education,Wuhan University,Wuhan 430072,China [2]College of Chemistry,Central China Normal University,Wuhan 430079,China

出　　处：《Science China Chemistry》2024年第11期3662-3668,共7页中国科学（化学英文版）

基　　金：supported by the National Key R&D Program of China (2022YFA1506100);the National Natural Science Foundation of China (21901191);the Fundamental Research Funds for the Central Universities (2042023kf0202);the China Postdoctoral Science Foundation (2023TQ0250)。

摘　　要：Previous carbene insertion to C–H bonds of 1,3-azoles relied on metal carbene species. Herein, we report a metal-free C(sp^(2))–H bond functionalization of 1,3-azoles with trifluoroacetylsilanes. The reaction features mild conditions, broad substrate scope and wide functional group tolerance. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trifluoroacetylsilanes under the photocatalyzed conditions: generating carbenes which undergo cyclopropanation and generating biradicals which promote ring-opening aromatization of the in situ generated fused cyclopropanes.

关 键 词：C(sp^(2))–H bond functionalization CARBENES BIRADICALS CYCLOPROPANATION brook rearrangement 

分 类 号：O621.251[理学—有机化学] O644.1[理学—化学]