Reductive methylation of primary and secondary amines and amino acids by aqueous formaldehyde and zinc

RA da Silva, IHS Estevam, LW Bieber

Index: da Silva, Renato A.; Estevam, Idalia H.S.; Bieber, Lothar W. Tetrahedron Letters, 2007 , vol. 48, # 43 p. 7680 - 7682

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Citation Number: 31

Abstract

Especially metallic zinc is a cheap and safe electron source, recently rediscovered in mild and efficient aqueous Barbier–Grignard type alkylations. 5 During our recent studies on the zinc promoted aminomethylation of alkyl halides, 6 the formation of N-methylated tertiary amines as side products in some cases prompted us to explore this process for the simple, general, and selective N-methylation of primary and secondary amines. The generally accepted mechanism involves in the first ...