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Synlett 2012; 23(20): 2869-2874
DOI: 10.1055/s-0032-1317545
DOI: 10.1055/s-0032-1317545
synpacts
Alkynes and Azides: Not Just for Click Reactions
Weitere Informationen
Publikationsverlauf
Received: 26. September 2012
Accepted after revision: 19. Oktober 2012
Publikationsdatum:
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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