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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

ABSTRACT: The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C-C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important ?-fluoroalkyl ketones from simple starting materials.

SUBMITTER: Zhao X

PROVIDER: S-EPMC6113317 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

Zhao Xian X Tu Hai-Yong HY Guo Lei L Zhu Shengqing S Qing Feng-Ling FL Chu Lingling L

Nature communications 20180828 1

The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving ...[more]

PMID: 30154495

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