BF3-Promoted, Carbene-like, C–H Insertion Reactions of Benzynes,Journal of the American Chemical Society

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BF3-Promoted, Carbene-like, C–H Insertion Reactions of Benzynes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-11-01 , DOI: 10.1021/jacs.8b10206
Hang Shen ₁ , Xiao Xiao ₁ , Moriana K. Haj ₁ , Patrick H. Willoughby ₁ , Thomas R. Hoye ₁

Affiliation

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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