Direct formylation of phenols using difluorocarbene as a safe CO surrogate

Org Biomol Chem. 2023 Jan 25;21(4):728-731. doi: 10.1039/d2ob02128e.

Abstract

A convenient method to prepare aryl formates is reported herein that exploits difluorocarbene to serve as a CO surrogate. This reaction is proposed to occur through a sequential O-difluoromethylation of phenol, followed by α-C-F bond functionalization of the resulting aryl difluoromethyl ether intermediate by phenol or moisture through fluorosemiacetal or orthoformate intermediates. Late-stage modification of biologically and materially active compounds is demonstrated.