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

SY Zhang, G He, WA Nack, Y Zhao, Q Li…

Index: He, Gang; Zhao, Yingsheng; Zhang, Shuyu; Lu, Chengxi; Chen, Gong Journal of the American Chemical Society, 2012 , vol. 134, # 1 p. 3 - 6

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Citation Number: 170

Abstract

We report an efficient method for the alkylation of γ-C (sp3)–H bonds of picolinamide- protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag2CO3 and dibenzyl phosphate,(BnO) 2PO2H, 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.