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Transition-metal-free alkynylation of aryl chlorides.

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 alcohol functionalities are compatible with the reaction conditions.

SUBMITTER: Truong T 

PROVIDER: S-EPMC3155656 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Transition-metal-free alkynylation of aryl chlorides.

Truong Thanh T   Daugulis Olafs O  

Organic letters 20110725 16

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 co  ...[more]

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