tert -Butyl peroxide (TBHP)/KI-mediated dual C(sp 2 )–H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines

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tert -Butyl peroxide (TBHP)/KI-mediated dual C(sp 2 )–H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines

Zhang, Tian-Shu; Zhang, Hongping; Fu, Rong; Wang, Jianyi; Hao, Wen-Juan; Tu, Shu-Jiang; Jiang, Bo

Chemical communications (Cambridge, England), 10/2019, Volume: 55, Issue: 88

Journal Article

A new radical-induced dehydrogenative heterocyclization of arylamines with α-diazo carbonyls has been established under metal-free oxidative conditions, enabling two-fold C(sp 2 )–H bond amination to access a wide range of functionalized 1,2,4-triazine derivatives with generally good yields by combining KI/ tert -butyl peroxide (TBHP). The present protocol features wide substrate scope, commercial accessibility, and mild reaction conditions. Mechanistic details of this radical process are rendered by conducting systematic theoretical calculations.

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