Copper-catalyzed Ullmann coupling under ligand-and additive-free conditions. Part 1: O-Arylation of phenols with aryl halides

…, S Chee, S Mak, P Buranaprasertsuk, W Chavasiri…

Index: Chang, Joyce Wei Wei; Chee, Sheena; Mak, Shiya; Buranaprasertsuk, Pongchart; Chavasiri, Warinthorn; Chan, Philip Wai Hong Tetrahedron Letters, 2008 , vol. 49, # 12 p. 2018 - 2022

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Citation Number: 51

Abstract

O-Arylation of a wide variety of substituted phenols and aliphatic alcohols with aryl halides catalyzed by copper iodide under mild ligand and additive free conditions ( n Bu 4 NBr, DMF, K 3 PO 4 , reflux, 22 h) is accomplished in good to excellent product yields (up to 95%). ... Unless otherwise stated, all reactions were run for 22 h at reflux with CuI/ n Bu 4 NBr/1a/2a/K 3 PO 4 ratio of 1:1:10:10:20 in the solvent. ... Reaction carried out with 5 mol % CuI and n Bu 4 NBr.