Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2

Israel González; Jesús Mosquera; César Guerrero; Ramón Rodríguez; Jacobo Cruces

doi:10.1021/ol802882k

Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2

Org Lett. 2009 Apr 16;11(8):1677-80. doi: 10.1021/ol802882k.

Authors

Israel González¹, Jesús Mosquera, César Guerrero, Ramón Rodríguez, Jacobo Cruces

Affiliation

¹ GalChimia, S.L. R&D Department, Cebreiro s/n 15823 O Pino, A Coruna, Spain.

PMID: 19354317
DOI: 10.1021/ol802882k

Abstract

N-Methylanilines are readily synthesized in high yields through the copper(II)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.

MeSH terms

Aniline Compounds / chemical synthesis*
Aniline Compounds / chemistry
Boron Compounds / chemistry*
Catalysis
Combinatorial Chemistry Techniques*
Copper / chemistry*
Methylation
Molecular Structure

Substances

Aniline Compounds
Boron Compounds
Copper
methaneboronic acid
methylaniline