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Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes
Author(s) -
Hyatt I. F. Dempsey,
Croatt Mitchell P.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203062
Subject(s) - hypervalent molecule , azide , chemistry , combinatorial chemistry , sulfoxide , cyclopropanation , medicinal chemistry , organic chemistry , catalysis , reagent
HIAT me, baby, one more time : Cyanocarbenes have been formed by the reaction of azides with hypervalent iodonium alkynyl triflates (HIATs). Experimental evidence supports the potential intermediacy of an azide‐substituted vinylidene or alkynyl azide, both of which could form a cyanocarbene. Trapping of the vinylidene and cyanocarbene includes OH insertion, dimethyl sulfoxide coordination, and cyclopropanation reactions.