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Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides

Daniel A. Everson, Brittany A. Jones and Daniel J. Weix*

*Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States, Email: daniel.weixrochester.edu

D. A. Everson, B. A. Jones, D. J. Weix, J. Am. Chem. Soc., 2012, 134, 6146-6159.

DOI: 10.1021/ja301769r (free Supporting Information)



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Abstract

In the presence of a Ni catalyst and Zn, various aryl and vinyl bromides are reductively coupled with alkyl bromides in high yields. Under similar conditions, activated aryl chlorides can also be coupled with bromoalkanes. The protocols are highly functional-group tolerant, and the reactions are assembled on the benchtop with no special precautions to exclude air or moisture.

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Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides

D. A. Everson, R. Shrestha, D. J. Weix, J. Am. Chem. Soc., 2010, 132, 920-921.


Key Words

Arenes, Zinc


ID: J48-Y2012-1130