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 journalArticle

197 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 languageEnglish (US)
Pages (from-to)2174-2177
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number7
DOIs
StatePublished - Mar 2 2016
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Cornella, J., Edwards, J. T., Qin, T., Kawamura, S., Wang, J., Pan, C. M., Gianatassio, R., Schmidt, M., Eastgate, M. D., & Baran, P. S. (2016). Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters. Journal of the American Chemical Society, 138(7), 2174-2177. https://doi.org/10.1021/jacs.6b00250