Sonogashira reactions with propyne: Facile synthesis of 4-hydroxy-2-methylbenzofurans from iodoresorcinols

MA Berliner, EM Cordi, JR Dunetz…

Index: Berliner, Martin A.; Cordi, Eric M.; Dunetz, Joshua R.; Price, Kristin E. Organic Process Research and Development, 2010 , vol. 14, # 1 p. 180 - 187

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Citation Number: 18

Abstract

The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols and terminal alkynes, including propyne, to give 4-hydroxy-2-substituted benzofurans. In particular, we describe the screening, method development, and scaleup of the reaction with propyne ...