Diastereoselective hydrogenation of arenes and pyridines using supported ruthenium nanoparticles under mild conditions

Abstract

A convenient and practical diastereoselective cis-hydrogenation of multi-substituted pyridines and arenes is reported.

Teaching an Old Dog New Tricks: Simple Selective and Regiodivergent Quinoline Hydrogenation

“…Following our recent contributions to the field, ,,− we became interested in developing a methodology for the direct synthesis of less common cis -decahydroquinoline substrates operating under mild reaction conditions. Considering the competence (and comparably low price) of ruthenium for hydrogenation reactions as well as, from a sustainable perspective, the efficient recovery and potential reuse of heterogeneous catalysts from reaction mixtures, we initiated our investigations with the screening of commercially available ruthenium on carbon.…”

Access to C(sp3) borylated and silylated cyclic molecules: hydrogenation of corresponding arenes and heteroarenes

“…General procedure B was followed with tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (1l) (174 mg, 0.5 mmol), 5% Rh/C (25 mg, 2 mol%) for 16 h. Aer purication solvent was removed by rotary evaporation to yield a colorless oil (170 mg, 97% yield). 1 9 however that report only tabulated data for one rotamer although both the rotamers are observed in the spectrum. 21 2-Cyclohexyl-4,…”

“…Hydrogenation of arenes and heteroarenes have been carried out in the past via transition metal (Pd, Ru, Pt and Rh) catalysis. [9][10][11][12][13][14][15][16][17][18][19][20] However, none of these reports demonstrated the hydrogenation on borylated or silylated arenes or heteroarenes. On this front, Glorius and coworkers pioneered the catalytic heterogeneous hydrogenation of boryl-and silyl-arenes/heteroarenes by a cyclic (alkyl)(amino) carbene rhodium complexes (Fig.…”

Piperidine: A Versatile Heterocyclic Ring for Developing Monoamine Oxidase Inhibitors

“…A modified Birch reduction using sodium in ethanol can also reduce pyridine to piperidine. Figure explains some important reactions for the synthesis of piperidine nuclei from different sources. ,− Hence, numerous efforts have been made over the years to create new techniques for the synthesis of piperidine-containing molecules …”