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

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 combi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-10, Vol.55 (88), p.13231-13234
Main Authors: Zhang, Tian-Shu, Zhang, Hongping, Fu, Rong, Wang, Jianyi, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Amines
Carbonyls
Crystallography
Dehydrogenation
Hydrogen bonds
Organic compounds
Substrates
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc07236e