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

Josep Cornellà(Scripps Research Institute), Jacob T. Edwards(Scripps Research Institute), Tian Qin(Scripps Research Institute), Shuhei Kawamura(Scripps Research Institute), Jie Wang(Scripps Research Institute), Chung‐Mao Pan(Scripps Research Institute), Ryan Gianatassio(Scripps Research Institute), Michael A. Schmidt(Bristol-Myers Squibb (United States)), Martin D. Eastgate(Bristol-Myers Squibb (United States)), Phil S. Baran(Scripps Research Institute)
Journal of the American Chemical Society
February 2, 2016
Cited by 459Open Access
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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.


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