Regioselective Synthesis of Tetraalkynylarenes by Consecutive Dual Sonogashira Coupling Reactions of the Bis(triflate) of 4,5-Diiodobenzene-1,2-diol

Authors

Thomas J. Fisher, University of Nebraska–LincolnFollow
Patrick H. Dussault, University of Nebraska-LincolnFollow

Date of this Version

5-2012

Citation

European Journal of Organic Chemistry 2012:14 (May 2012), pp. 2831–2836; doi: 10.1002/ejoc.201200079

Comments

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Used by permission.

Abstract

Abstract The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar–I linkages. Subsequent coupling reactions at the Ar–OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.