Cu-Catalyzed Three-Component Carboamination of Alkenes

Samuel N. Gockel; Travis L. Buchanan; Kami L. Hull

doi:10.1021/jacs.7b10529

Cu-Catalyzed Three-Component Carboamination of Alkenes

Samuel N. Gockel, Travis L. Buchanan, Kami L. Hull

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	58-61
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	140
Issue number	1
DOIs	https://doi.org/10.1021/jacs.7b10529
State	Published - Jan 10 2018

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "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.",

author = "Gockel, {Samuel N.} and Buchanan, {Travis L.} and Hull, {Kami L.}",

note = "Funding Information: The authors thank the NIH (1R35GM125029), the Sloan Research Foundation, and the University of Illinois for their generous support of this work. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2018",

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AU - Gockel, Samuel N.

AU - Buchanan, Travis L.

AU - Hull, Kami L.

N1 - Funding Information: The authors thank the NIH (1R35GM125029), the Sloan Research Foundation, and the University of Illinois for their generous support of this work. Publisher Copyright: © 2017 American Chemical Society.

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Y1 - 2018/1/10

N2 - 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.

AB - 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.

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Cu-Catalyzed Three-Component Carboamination of Alkenes

Abstract

ASJC Scopus subject areas

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