Organic letters

Transition-Metal-Free Alkynylation of Aryl Chlorides

T Truong, O Daugulis

Index: Truong, Thanh; Daugulis, Olafs Organic Letters, 2011 , vol. 13, # 16 p. 4172 - 4175

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Citation Number: 21

Abstract

Two sets of conditions have been developed for a base-mediated, transition-metal-free alkynylation of aryl chlorides that proceeds via benzyne intermediates. The first set of conditions involves the use of TMPLi base in a pentane/THF mixture at 25° C. The second set involves use of a metal alkoxide base in dioxane at elevated temperature. Reasonable functional group tolerance has been observed. Fluoro, trifluoromethyl, silyl, cyano, and ...