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Cu-Catalyzed Three-Component Carboamination of Alkenes.

ABSTRACT: Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening to forge the C-N bond.

SUBMITTER: Gockel SN

PROVIDER: S-EPMC6092015 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Cu-Catalyzed Three-Component Carboamination of Alkenes.

Gockel Samuel N SN Buchanan Travis L TL Hull Kami L KL

Journal of the American Chemical Society 20171228 1

Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening ...[more]

PMID: 29095598

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