Transition-metal-free alkynylation of aryl chlorides.

Thanh Truong, Olafs Daugulis

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

Organic letters 2011 Aug 19

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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 alcohol functionalities are compatible with the reaction conditions. © 2011 American Chemical Society