Work

Transition-Metal-Free Alkynylation of Aryl Chlorides

Year: 2011

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol2014736

Authors: Thanh Truong, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: New Methods for Direct Carbon-Hydrogen Bond Functionalization