BF3‑Promoted, Carbene-like, C–H Insertion Reactions of Benzynes

BF3‑Promoted, Carbene-like, C–H Insertion Reactions of Benzynes

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 rep...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-11, Vol.140 (46), p.15616-15620
Main Authors: Shen, Hang, Xiao, Xiao, Haj, Moriana K, Willoughby, Patrick H, Hoye, Thomas R
Format: Article
Language:eng
Online Access:Get full text
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Summary: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.
ISSN:0002-7863
1520-5126