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Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement

Wei Zhao, Ryan P. Wurz , Jonas C. Peters* and Gregory C. Fu*

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

W. Zhao, R. P. Wurz, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 12153-12156.

DOI: 10.1021/jacs.7b07546 (free Supporting Information)


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Abstract

A safe alternative to the Curtius rearrangement, that employs a copper catalyst in combination with blue-LED irradiation, achieves a decarboxylative coupling of readily available aliphatic N-hydroxyphthalimide esters to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including alcohols, aldehydes, epoxides, indoles, nitroalkanes, and sulfides.

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proposed mechanism



Key Words

protected primary amines, phthalimides


ID: J48-Y2017