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Updated: Aug 11, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
AIBN as an Electrophilic Reagent for Cyano Group Transfer
Quintin Elliott1, Igor V Alabugin1
1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
Abstract:
AIBN is a convenient electrophilic cyanation reagent for transforming ArLi into ArCN under mild conditions. The addition/fragmentation cascade is controlled by Li···N chelation in which AIBN nitrogens assist in the nearly barrierless fragmentation into the desired ArCN product. Acidic C-H bonds in the fragmented byproduct partially consume ArLi by protonation. Density functional theory calculations and isotopic labeling probe the mechanism and explain the switch to substituted hydrazones in reactions with BuLi.
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