N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer

Qing Xia; Hao Tian; Jianyang Dong; Yi Qu; Lili Li; Hongjian Song; Yuxiu Liu; Qingmin Wang

doi:10.1002/chem.201801886

N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer

Chemistry. 2018 Jul 2;24(37):9269-9273. doi: 10.1002/chem.201801886. Epub 2018 May 30.

Authors

Qing Xia¹, Hao Tian¹, Jianyang Dong¹, Yi Qu¹, Lili Li¹, Hongjian Song¹, Yuxiu Liu¹, Qingmin Wang^{1

2}

Affiliations

¹ State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China.
² Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, P. R. China.

PMID: 29761880
DOI: 10.1002/chem.201801886

Abstract

A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Brønsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.

Keywords: ketyl radical; photoredox catalysis; proton-coupled electron transfer; radical reactions; α-amino radicals.