Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes

Abstract

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 OH insertion, dimethyl sulfoxide coordination, and cyclopropanation reactions. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.