Electroreductive Methylation of Primary and Secondary Amines

Electroreductive Methylation of Primary and Secondary Amines

Silva, Renato A. da; Souza, Ronny F. M. de; Areias, Madalena C. C.; Navarro, Marcelo; Bieber, Lothar W.

Abstract:

A new synthetic method of reductive methylation promoted by electrolysis in aqueous medium was studied in this work. The method is based on the reduction of iminium ions generated in situ from the condensation of amines with formaldehyde. Besides the classical Leuckart-Wallach or Eschweiler-Clarke procedures, this reaction is normally performed in organic solvents using several borohydride reagents or catalytic hydrogenation. We decided to study the electrorreductive methylation reaction, by means of aqueous formaldehyde motivated by the good results of our reaction promoted by zinc and due to the scarce reports on the electrochemical strategy in the literature.

A new synthetic method of reductive methylation promoted by electrolysis in aqueous medium was studied in this work. The method is based on the reduction of iminium ions generated in situ from the condensation of amines with formaldehyde. Besides the classical Leuckart-Wallach or Eschweiler-Clarke procedures, this reaction is normally performed in organic solvents using several borohydride reagents or catalytic hydrogenation. We decided to study the electrorreductive methylation reaction, by means of aqueous formaldehyde motivated by the good results of our reaction promoted by zinc and due to the scarce reports on the electrochemical strategy in the literature.

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DOI: 10.5151/chempro-14bmos-R0203-1

Referências bibliográficas

• [1] 1 Moore, M. L. Organic Reactions 1949, 5, 301-303.
• [2] 2 Baxter, E. W.; Reitz, A. B. Organic Reactions 2002, 59, 1-714.
• [3] 3 Emerson, W. S. Organic Reactions 1948, 4, 174-255.
• [4] 4 Silva, R. A.; Bieber, L. W.; Estevam, I. H. S. Tetrahedron Letters 2007, 48, 7680-7682.
• [5] 5 Lund, H. Acta Chem. Scand. 1959, 13, 249.
• [6] 6 Smirnov, Y.; Fedorova, L. A.; Tomilov, A. P. Soviet electrochemistry 1992, 28 (4), 476-484.

Como citar:

Silva, Renato A. da; Souza, Ronny F. M. de; Areias, Madalena C. C.; Navarro, Marcelo; Bieber, Lothar W.; "Electroreductive Methylation of Primary and Secondary Amines", p-203-203. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0203-1