Radical O→ C transposition: A metal-free process for conversion of phenols into benzoates and benzamides

A Baroudi, J Alicea, P Flack, J Kirincich…

Index: Baroudi, Abdulkader; Alicea, Jeremiah; Flack, Phillip; Kirincich, Jason; Alabugin, Igor V. Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1521 - 1537

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Citation Number: 32

Abstract

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the C S moiety. This addition step, analogous to the first step of the Barton− McCombie reaction, produces a carbon radical which undergoes 1, 2 O→ C transposition ...

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