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 journalArticlepeer-review

17 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 languageEnglish (US)
Pages (from-to)15616-15620
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number46
DOIs
StatePublished - Nov 21 2018

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

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