Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp(3)-sp(2) Cross-Coupling of Oxalates with Aryl Halides

作者:Zhang Xiaheng; MacMillan David W C
来源:Journal of the American Chemical Society, 2016, 138(42): 13862-13865.
DOI:10.1021/jacs.6b09533

摘要

Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral C-sp(3)-C-sp(2) cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.

  • 出版日期2016-10-26