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Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides

Alexander C. Wotal and Daniel J. Weix*

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

A. C. Wotal, D. J. Weix, Org. Lett., 2012, 14, 1363-1365.

DOI: 10.1021/ol300217x (free Supporting Information)

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Unsymmetrical dialkyl ketones can be prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. Various functional groups are tolerated, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed.

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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

Acylation, Manganese

ID: J54-Y2012-0780