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Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines

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Promoted by iodide anion the rhodium complex dimer, [Cp*RhCl2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6‐tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH‐Et3N) mixture at 40 °C, with catalyst loadings as low as 0.005 mol% being feasible.
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Document Type: Communications

Affiliations: 1: Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K., (~jxiao), Fax: (+44)-151-794-3588, URL: 2: Chemical R & D, Global Research & Development, Pfizer, Sandwich, Kent CT13 9NJ, U.K.

Publication date: 14 January 2013

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