Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

Josep Cornella; Jacob T. Edwards; Tian Qin; Shuhei Kawamura; Jie Wang; Chung Mao Pan; Ryan Gianatassio; Michael Schmidt; Martin D. Eastgate; Phil S. Baran

doi:10.1021/jacs.6b00250

Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

Josep Cornella, Jacob T. Edwards, Tian Qin, Shuhei Kawamura, Jie Wang, Chung Mao Pan, Ryan Gianatassio, Michael Schmidt, Martin D. Eastgate, Phil S. Baran

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

328 Scopus citations

Abstract

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl₂·6H₂O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

Original language	English (US)
Pages (from-to)	2174-2177
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	7
DOIs	https://doi.org/10.1021/jacs.6b00250
State	Published - Mar 2 2016
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b00250

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title = "Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters",

abstract = "A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.",

author = "Josep Cornella and Edwards, {Jacob T.} and Tian Qin and Shuhei Kawamura and Jie Wang and Pan, {Chung Mao} and Ryan Gianatassio and Michael Schmidt and Eastgate, {Martin D.} and Baran, {Phil S.}",

note = "Funding Information: Financial support for this work was provided by NIH (GM-097444), Bristol-Myers Squibb, Department of Defense (NDSEG fellowship to J.T.E.), and Catalan Government (Postdoctoral Fellowship to J.C.). We thank Prof. A. L. Rheingold and Dr. C. E. Moore for X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/jacs.6b00250",

language = "English (US)",

volume = "138",

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AU - Cornella, Josep

AU - Edwards, Jacob T.

AU - Qin, Tian

AU - Kawamura, Shuhei

AU - Wang, Jie

AU - Pan, Chung Mao

AU - Gianatassio, Ryan

AU - Schmidt, Michael

AU - Eastgate, Martin D.

AU - Baran, Phil S.

N1 - Funding Information: Financial support for this work was provided by NIH (GM-097444), Bristol-Myers Squibb, Department of Defense (NDSEG fellowship to J.T.E.), and Catalan Government (Postdoctoral Fellowship to J.C.). We thank Prof. A. L. Rheingold and Dr. C. E. Moore for X-ray crystallographic analysis. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/3/2

Y1 - 2016/3/2

N2 - A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

AB - A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

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Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

Abstract

ASJC Scopus subject areas

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