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Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides

Kierra M. M. Huihui, Jill A. Caputo, Zulema Melchor, Astrid M. Olivares, Amanda M. Spiewak, Keywan A. Johnson, Tarah A. DiBenedetto, Seoyoung Kim, Laura K. G. Ackerman and Daniel J. Weix*

*Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States, Email: daniel.weixrochester.edu

K. M. M. Huihui, J. A. Caputo, Z. Melchor, A. M. Olivares, A. M. Spiewak, K. A. Johnson, T. A. DiBenedetto, S. Kim, L. K. G. Ackerman, D. J. Weix, J. Am. Chem. Soc., 2016, 138, 5016-5019.

DOI: 10.1021/jacs.6b01533 (free Supporting Information)


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Abstract

In a decarboxylative coupling of alkyl N-hydroxyphthalimide esters with aryl iodides in the presence of a nickel catalyst and Zn as reducing agent, no photocatalyst, light, or arylmetal reagent is needed to form alkyl radicals from the carboxylic acid derivative. Methyl, primary, and secondary alkyl groups can all be coupled in good yield.

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Key Words

alkylation, Zn


ID: J48-Y2016