Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Organic Letters
Alexander C Wotal, Daniel J Weix

Abstract

Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)(2) intermediate with the carboxylic acid derivative.

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Citations

Nov 22, 2014·Journal of the American Chemical Society·Chenglong ZhaoHegui Gong
Sep 24, 2014·Journal of the American Chemical Society·Alan H Cherney, Sarah E Reisman
May 14, 2014·The Journal of Organic Chemistry·Daniel A Everson, Daniel J Weix
Aug 11, 2015·Journal of the American Chemical Society·Nathaniel T Kadunce, Sarah E Reisman
Apr 1, 2016·Journal of the American Chemical Society·Kierra M M HuihuiDaniel J Weix
Sep 2, 2015·Journal of the American Chemical Society·Xuan WangHegui Gong
Aug 31, 2016·Topics in Current Chemistry·Xuan WangHegui Gong
Aug 21, 2013·Journal of the American Chemical Society·Soumik Biswas, Daniel J Weix
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