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Selective Monomethylation of Anilines by Cu(OAc)2-Promoted Cross-Coupling with MeB(OH)2

Israel González, Jesús Mosquera, César Guerrero, Ramón Rodríguez and Jacobo Cruces*

*GalChimia, S.L. R&D Department, Cebreiro s/n 15823 O Pino, A Coruńa, Spain, Email: jacobo.crucesgalchimia.com

I. González, J. Mosquera, C. Guerrero, R. Rodríguez, Jacobo Cruces, Org. Lett., 2009, 11, 1677-1680.

DOI: 10.1021/ol802882k (free Supporting Information)


Abstract

A Chan-Lam coupling using methylboronic acid enables a selective monomethylation of anilines. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid. N-Methylanilines are synthesized in good yields.

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Selective Copper-Promoted Cross-Coupling of Aromatic Amines with Alkyl Boronic Acids

M. Larrosa, C. Guerrero, R. Rodríguez, J. Cruces, Synlett, 2010, 2101-2105.


Key Words

Chan-Lam Coupling, Anilines


ID: J54-Y2009-1240