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

Hang Shen; Xiao Xiao; Moriana K. Haj; Patrick H. Willoughby; Thomas R. Hoye

doi:10.1021/jacs.8b10206

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

Hang Shen
, Xiao Xiao
, Moriana K. Haj
, Patrick H. Willoughby
, Thomas R. Hoye

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

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.

Original language	English (US)
Pages (from-to)	15616-15620
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	46
DOIs	https://doi.org/10.1021/jacs.8b10206
State	Published - Nov 21 2018

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

Publisher link

10.1021/jacs.8b10206

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6386166

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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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AU - Hoye, Thomas R.

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