Synlett
DOI: 10.1055/s-0036-1590905
letter
© Georg Thieme Verlag Stuttgart · New York

TBHP/n-Bu4PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

Mehdi Adib*, Rahim Pashazadeh
  • School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Email: madib@khayam.ut.ac.ir
This research was supported by the Research Council of University of Tehran.
Further Information

Publication History

Received: 16 June 2017

Accepted after revision: 19 August 2017

Publication Date:
15 September 2017 (eFirst)

Abstract

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C–O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert-butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

Supporting Information