Journal of the American Chemical Society 2016-02-24

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

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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.