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BF3-Promoted, Carbene-like, C-H Insertion Reactions of Benzynes. 2018

Hang Shen, and Xiao Xiao, and Moriana K Haj, and Patrick H Willoughby, and Thomas R Hoye
Department of Chemistry , University of Minnesota , 207 Pleasant Street , SE Minneapolis , Minnesota 55455 , United States.

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.

UI MeSH Term Description Entries
D008697 Methane The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed)
D001880 Boranes The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed) Borane,Boron Hydride,Boron Hydrides,Hydride, Boron,Hydrides, Boron
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D001555 Benzene Derivatives Organic compounds derived from BENZENE. Derivatives, Benzene
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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