Convenient Procedure for the α-Methylation of Simple Pyridines

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Abstract:

A convenient and straightforward laboratory procedure is presented for a highly selective mono-α-methylation of pyridines without reactive functional groups. The methylating agent is probably carbon monoxide/dihydrogen generated in situ from a high-boiling alcohol on a metal surface. The reaction is catalyzed by a Raney nickel catalyst at ambient pressure, which renders the protocol practicable in standard organic laboratories. The intrinsically high reaction temperature and long reaction times restrict the application to pyridine derivatives with less reactive substituents. The outcome of the reaction can be rationalized by the assumption of a simple heterogeneous mechanism.

Keywords: Electrophilic substitution; Raney nickel catalyst; pyridines; α-methylation

Document Type: Research Article

DOI: http://dx.doi.org/10.1080/00397910802213745

Affiliations: Fachbereich Chemie, Philipps-Universitat Marburg, Marburg, Germany

Publication date: January 1, 2008

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