Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2.
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.
González
Israel
I
GalChimia, S.L. R&D Department, Cebreiro s/n 15823 O Pino, A Coruna, Spain.
Mosquera
Jesús
J
Guerrero
César
C
Rodríguez
Ramón
R
Cruces
Jacobo
J
D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure
D000814:Aniline Compounds; D001896:Boron Compounds; D003300:Copper; C116999:methaneboronic acid; C021313:methylaniline