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

Online availability

10.1021/jacs.7b10529

Library availability

Discover UIUC Full Text

Cite this

@article{92223de62de746d4bf54b064ed86cd47,

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",

month = jan,

day = "10",

doi = "10.1021/jacs.7b10529",

language = "English (US)",

volume = "140",

pages = "58--61",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Cu-Catalyzed Three-Component Carboamination of Alkenes

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.

PY - 2018/1/10

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.

UR - http://www.scopus.com/inward/record.url?scp=85040327185&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85040327185&partnerID=8YFLogxK

U2 - 10.1021/jacs.7b10529

DO - 10.1021/jacs.7b10529

M3 - Article

C2 - 29095598

AN - SCOPUS:85040327185

VL - 140

SP - 58

EP - 61

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 1

ER -

Cu-Catalyzed Three-Component Carboamination of Alkenes

Abstract

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this