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Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

ABSTRACT: Herein we report a facile, mild reaction protocol to form carbon-carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with ?-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10-20?mol?%) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36-87?%). DFT studies were used to elucidate the mechanism for this alkenylation reaction.

SUBMITTER: Dasgupta A

PROVIDER: S-EPMC7497215 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

Dasgupta Ayan A Stefkova Katarína K Babaahmadi Rasool R Gierlichs Lukas L Ariafard Alireza A Melen Rebecca L RL

Angewandte Chemie (International ed. in English) 20200715 36

Herein we report a facile, mild reaction protocol to form carbon-carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10-20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36-87 %). DFT studies were used to elucidate the mechanism for this alkenylation reacti ...[more]

PMID: 32485034

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