Synlett 2012; 23(20): 2869-2874
DOI: 10.1055/s-0032-1317545
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© Georg Thieme Verlag Stuttgart · New York

Alkynes and Azides: Not Just for Click Reactions

I. F. Dempsey Hyatt
Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Sullivan Science Building, PO Box 26170, Greensboro, NC 27402, USA   Fax: +1(336)3345402   Email: mpcroatt@uncg.edu
,
Maria Elena Meza-Aviña
Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Sullivan Science Building, PO Box 26170, Greensboro, NC 27402, USA   Fax: +1(336)3345402   Email: mpcroatt@uncg.edu
,
Mitchell P. Croatt*
Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Sullivan Science Building, PO Box 26170, Greensboro, NC 27402, USA   Fax: +1(336)3345402   Email: mpcroatt@uncg.edu
› Author Affiliations
Further Information

Publication History

Received: 26 September 2012

Accepted after revision: 19 October 2012

Publication Date:
19 November 2012 (online)

Abstract

We recently reported two unexplored reactivities of alkynes and azides. The first method reacts nucleophilic alkynes and electrophilic azides to synthesize sulfonyl-substituted 1,5-disubstituted 1,2,3-triazoles. The second method reacts electrophilic alkynes with nucleophilic azides to form alkynyl azides that immediately extrude dinitrogen to form cyanocarbenes which were trapped by O–H insertion, sulfoxide complexation, and cyclopropanation. The design and discovery of these reactions, along with key observations, is discussed herein.

 
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