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Decarboxylative Hydroalkylation of Alkynes.

ABSTRACT: The merger of open- and closed-shell elementary organometallic steps has enabled the selective intermolecular addition of nucleophilic radicals to unactivated alkynes. A range of carboxylic acids can be subjected to a CO2 extrusion, nickel capture, migratory insertion sequence with terminal and internal alkynes to generate stereodefined functionalized olefins. This platform has been further extended, via hydrogen atom transfer, to the direct vinylation of unactivated C-H bonds. Preliminary studies indicate that a Ni-alkyl migratory insertion is operative.

SUBMITTER: Till NA

PROVIDER: S-EPMC6607893 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Decarboxylative Hydroalkylation of Alkynes.

Till Nicholas A NA Smith Russell T RT MacMillan David W C DWC

Journal of the American Chemical Society 20180420 17

The merger of open- and closed-shell elementary organometallic steps has enabled the selective intermolecular addition of nucleophilic radicals to unactivated alkynes. A range of carboxylic acids can be subjected to a CO<sub>2</sub> extrusion, nickel capture, migratory insertion sequence with terminal and internal alkynes to generate stereodefined functionalized olefins. This platform has been further extended, via hydrogen atom transfer, to the direct vinylation of unactivated C-H bonds. Prelim ...[more]

PMID: 29664294

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