Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines  via  Rhodium‐Catalyzed Transfer Hydrogenation | Zendy

Wu Jianjun | Zendy; Tang Weijun | Zendy; Pettman Alan | Zendy; Xiao Jianliang | Zendy

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Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines via Rhodium‐Catalyzed Transfer Hydrogenation

Author(s) -

Wu Jianjun,

Tang Weijun,

Pettman Alan,

Xiao Jianliang

Publication year - 2013

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201201034

Subject(s) - chemistry , pyridinium , rhodium , iodide , transfer hydrogenation , triethylamine , catalysis , formic acid , dimer , medicinal chemistry , pyridine , organic chemistry , combinatorial chemistry , ruthenium

Promoted by iodide anion the rhodium complex dimer, [Cp*RhCl 2 ] 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‐Et 3 N) mixture at 40 °C, with catalyst loadings as low as 0.005 mol% being feasible.

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