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Issue 88, 2019

tert-Butyl peroxide (TBHP)/KI-mediated dual C(sp2)–H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines

Author affiliations

Abstract

A new radical-induced dehydrogenative heterocyclization of arylamines with α-diazo carbonyls has been established under metal-free oxidative conditions, enabling two-fold C(sp2)–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.

Graphical abstract: tert-Butyl peroxide (TBHP)/KI-mediated dual C(sp2)–H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines

Supplementary files

Article information


Submitted
15 Sep 2019
Accepted
11 Oct 2019
First published
11 Oct 2019

Chem. Commun., 2019,55, 13231-13234
Article type
Communication

tert-Butyl peroxide (TBHP)/KI-mediated dual C(sp2)–H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines

T. Zhang, H. Zhang, R. Fu, J. Wang, W. Hao, S. Tu and B. Jiang, Chem. Commun., 2019, 55, 13231 DOI: 10.1039/C9CC07236E

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