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Updated: Jul 4, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes
Ryan D Baxter1, John Montgomery
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Abstract:
The nickel-catalyzed coupling of aldehydes, alkynes, and dialkylsilanes results in an unusual dehydrogenative cyclocondensation process to afford five-membered silacyclic products. The process allows dialkylsilanes to serve as a silylene synthetic equivalent. A mechanistic pathway for the process involving the formation of an aldehyde/alkyne-derived nickel metallacycle followed by sequential sigma-bond metathesis processes involving the two Si-H bonds has been proposed.
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