Issue 16, 2019

Electrochemically dehydrogenative C–H/P–H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1H)-ones and xanthenes

Abstract

An efficient electrochemical approach for the C(sp2)–H phosphonation of quinoxalin-2(1H)-ones and C(sp3)–H phosphonation of xanthenes has been developed. The chemistry was performed in an undivided cell under constant current conditions and features a wide range of substrates, up to 99% yield and it is free of transition-metal catalysts- and external oxidants, thereby providing a straightforward approach for dehydrogenative C–H/P–H cross-coupling. In addition, control experiments disclose that some of the reactions may involve a radical pathway.

Graphical abstract: Electrochemically dehydrogenative C–H/P–H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1H)-ones and xanthenes

Supplementary files

Article information

Article type
Paper
Submitted
05 May 2019
Accepted
12 Jul 2019
First published
12 Jul 2019

Green Chem., 2019,21, 4412-4421

Electrochemically dehydrogenative C–H/P–H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1H)-ones and xanthenes

K. Li, Y. Jiang, K. Xu, C. Zeng and B. Sun, Green Chem., 2019, 21, 4412 DOI: 10.1039/C9GC01474H

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