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. 2013 Feb 13;135(6):2124-7.
doi: 10.1021/ja312277g. Epub 2013 Jan 29.

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

Shu-Yu Zhang  1 , Gang He, William A Nack, Yingsheng Zhao, Qiong Li, Gong Chen
Affiliations

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

Shu-Yu Zhang et al. J Am Chem Soc. .

Abstract

We report an efficient method for the alkylation of γ-C(sp(3))-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag(2)CO(3) and dibenzyl phosphate, (BnO)(2)PO(2)H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

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