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Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature

Hien-Quang Do, Shoshana Bachman, Alex C. Bissember, Jonas C. Peters* and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: jpeterscaltech.edu, gcfucaltech.edu

H.-Q. Do, S. Bachman, A. C. Bissember, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2014, 136, 2162-2167.

DOI: 10.1021/ja4126609 (free Supporting Information)



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Abstract

A photoinduced, copper-catalyzed monoalkylation of primary amides couples a broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) with unactivated secondary (and hindered primary) alkyl bromides and iodides. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist.

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Key Words

Amides


ID: J48-Y2014