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. 2014 Feb 5;136(5):1789-92.
doi: 10.1021/ja413131m. Epub 2014 Jan 21.

Nickel-catalyzed site-selective alkylation of unactivated C(sp3)-H bonds

Xuesong Wu  1 , Yan Zhao, Haibo Ge
Affiliations

Nickel-catalyzed site-selective alkylation of unactivated C(sp3)-H bonds

Xuesong Wu et al. J Am Chem Soc. .

Erratum in

Abstract

The direct alkylation of unactivated sp(3) C-H bonds of aliphatic amides was achieved via nickel catalysis with the assist of a bidentate directing group. The reaction favors the C-H bonds of methyl groups over the methylene C-H bonds and tolerates various functional groups. Moreover, this reaction shows a predominant preference for sp(3) C-H bonds of methyl groups via a five-membered ring intermediate over the sp(2) C-H bonds of arenes in the cyclometalation step.

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