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

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 ?-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.

SUBMITTER: Shen H

PROVIDER: S-EPMC6386166 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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

Shen Hang H Xiao Xiao X Haj Moriana K MK Willoughby Patrick H PH Hoye Thomas R TR

Journal of the American Chemical Society 20181108 46

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. ...[more]

PMID: 30384597

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