Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature

…, S Bachman, AC Bissember, JC Peters…

Index: Do, Hien-Quang; Bachman, Shoshana; Bissember, Alex C.; Peters, Jonas C.; Fu, Gregory C. Journal of the American Chemical Society, 2014 , vol. 136, # 5 p. 2162 - 2167

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Citation Number: 30

Abstract

The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (ie, poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with ...