Electrocatalytic C-H/N-H Coupling of 2'-Aminoacetophenones for the Synthesis of Isatins

Peng Qian; Ji-Hu Su; Yukang Wang; Meixiang Bi; Zhenggen Zha; Zhiyong Wang

doi:10.1021/acs.joc.7b00635

Electrocatalytic C-H/N-H Coupling of 2'-Aminoacetophenones for the Synthesis of Isatins

J Org Chem. 2017 Jun 16;82(12):6434-6440. doi: 10.1021/acs.joc.7b00635. Epub 2017 Jun 2.

Authors

Peng Qian¹, Ji-Hu Su¹, Yukang Wang¹, Meixiang Bi¹, Zhenggen Zha¹, Zhiyong Wang¹

Affiliation

¹ Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology and ‡CAS Key Laboratory of Microscale Magnetic Resonance, Department of Modern Physics, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.

PMID: 28535683
DOI: 10.1021/acs.joc.7b00635

Abstract

2'-Aminoacetophenones undergo a C(sp³)-H oxidation followed by intramolecular C-N bond formation by virtue of a simple electrochemical oxidation in the presence of n-Bu₄NI, providing various isatins with moderate to good yields. The reaction intermediates were detected, and a radical-based pathway was proposed.

Publication types

Research Support, Non-U.S. Gov't