Flow Synthesis of 2-Methylpyridines via α-MethylationReportar como inadecuado




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1

College of Pharmacy, Faculty of Health Science, University of Manitoba, Winnipeg, MB R3E 0T6, Canada

2

Department of Chemistry, Faculty of Science, University of Manitoba, Winnipeg, MB R3T 2N2, Canada





*

Author to whom correspondence should be addressed.



Academic Editor: Kerry Gilmore

Abstract A series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney® nickel using a low boiling point alcohol 1-propanol at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanisms of the reaction is also presented which involves heterogeneous catalysis and-or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol. View Full-Text

Keywords: continuous flow; 2-methylpyridines; Raney® nickel; green chemistry; α-methylation; Ladenberg rearrangement; flow chemistry continuous flow; 2-methylpyridines; Raney® nickel; green chemistry; α-methylation; Ladenberg rearrangement; flow chemistry





Autor: Camille Manansala 1 and Geoffrey K. Tranmer 1,2,*

Fuente: http://mdpi.com/



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