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Indexed by:期刊论文

Date of Publication:2016-05-18

Journal:TETRAHEDRON LETTERS

Included Journals:SCIE、Scopus

Volume:57

Issue:20

Page Number:2143-2146

ISSN No.:0040-4039

Key Words:Sonogashira coupling; Glaser coupling; Transition-metal catalyst; 1,4-Disubstituted; 1,3-Butadiynes

Abstract:A simplified synthesis of symmetrical 1,4-disubstitued 1,3-butadiynes was developed using a sequential two-step process combining a typical Sonogashira coupling with a Glaser coupling. The Sonogashira reaction coupled arylbromide and trimethylsilylacetylene. In the second step, a Glaser coupling reaction was performed using the crude trimethyl(arylethynyl)silane product from the previous Sonogashira coupling in a basic solvent; the Glaser coupling proceeded to completion without the addition of extra Pd or Cu catalysts. The catalytic amount of metal (Cu and Pd) in the second step was substantially less than that used in a typical Glaser coupling reaction. (C) 2016 Elsevier Ltd. All rights reserved.