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

180 Citations (Scopus)

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

Fingerprint

Oxidation-Reduction
Esters
Substrates
Hinges
Carboxylic Acids
Catalysis
Carboxylic acids
Zinc
Derivatives
Catalysts

ASJC Scopus subject areas

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

Cite this

Cornella, J., Edwards, J. T., Qin, T., Kawamura, S., Wang, J., Pan, C. M., ... 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

Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters. / Cornella, Josep; Edwards, Jacob T.; Qin, Tian; Kawamura, Shuhei; Wang, Jie; Pan, Chung Mao; Gianatassio, Ryan; Schmidt, Michael; Eastgate, Martin D.; Baran, Phil S.

In: Journal of the American Chemical Society, Vol. 138, No. 7, 02.03.2016, p. 2174-2177.

Research output: Contribution to journalArticle

Cornella, J, Edwards, JT, Qin, T, Kawamura, S, Wang, J, Pan, CM, Gianatassio, R, Schmidt, M, Eastgate, MD & Baran, PS 2016, 'Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters', Journal of the American Chemical Society, vol. 138, no. 7, pp. 2174-2177. https://doi.org/10.1021/jacs.6b00250
Cornella, Josep ; Edwards, Jacob T. ; Qin, Tian ; Kawamura, Shuhei ; Wang, Jie ; Pan, Chung Mao ; Gianatassio, Ryan ; Schmidt, Michael ; Eastgate, Martin D. ; Baran, Phil S. / Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 7. pp. 2174-2177.
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