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Updated: Feb 3, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
BF3-Promoted, Carbene-like, C-H Insertion Reactions of Benzynes
Hang Shen1, Xiao Xiao1, Moriana K Haj1
1Department of Chemistry , University of Minnesota , 207 Pleasant Street , SE Minneapolis , Minnesota 55455 , United States.
Abstract:
Boron trifluoride is observed to promote a variety of C-H insertion reactions of benzynes bearing pendant alkyl groups. Computations and various mechanistic studies indicate that BF3 engages the strained π-bond to confer carbene-like character on the adjacent, noncoordinated benzyne carbon. This represents an unprecedented catalytic role for a non-transition metal such as BF3.
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