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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.

SUBMITTER: Cornella J

PROVIDER: S-EPMC4768290 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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

Cornella Josep J Edwards Jacob T JT Qin Tian T Kawamura Shuhei S Wang Jie J Pan Chung-Mao CM Gianatassio Ryan R Schmidt Michael M Eastgate Martin D MD Baran Phil S PS

Journal of the American Chemical Society 20160209 7

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) bo ...[more]

PMID: 26835704

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