Chemoselective reduction of heteroarenes with a reduced graphene oxide supported rhodium nanoparticle catalyst

Abstract

Rhodium nanoparticles immobilized on reduced graphene oxide catalyze the selective hydrogenation of N- and O-containing heteroarenes.

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

“…The hydrogenation of aza-heterocycles such as quinolines (35a), pyridines (110l), indole (88b) and oxa-heterocycle such as furan (326) was reported using a catalytic amount of RhNPs supported on rGO (Scheme 219) by Dyson et al using an ionic liquid as the reaction medium. 394 The hydrogenation of natural constituents having benzofurans such as visnagin, 8-methoxy psoralen, and khellin was achieved successfully using this catalyst with selective reduction of the furan rings. The catalyst was recycled up to ve times with 98-91% yield of 1,2,3,4tetrahyroquinolines.…”

Chemoselective reduction of quinoline over Rh–C60 nanocatalysts

“…A variety of heterogeneous catalysts have been developed to improve activity and selectivity for this reaction in recent years. Au, 17 Rh, [18][19][20][21][22][23][24][25] Ru, 26,27 Pd 28 and Pt 29 -based catalysts have revealed to be very active and selective. Specifically, Rh nanoparticles (NP) show high selectivity towards 1,2,3,4tetrahydroquinoline (2).…”

Scalable and Straightforward Synthesis of All Isomeric (Cyclo)alkylpiperidines

“…[19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] Recent works which implied the strategy shown in Scheme 1 used the Sonogashira cross-coupling, [36,37] Negishi [26] or Kumada [27] reactions with benzyl organometallics, aldol-type condensations, [27,38] or reactions of lithiated pyridines with aromatic aldehydes, [39] carboxylic acids or their derivatives [40,41] to introduce the substituent at the pyridine ring prior the hydrogenation (Scheme 2). [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] Recent works which implied the strategy shown in Scheme 1 used the Sonogashira cross-coupling, [36,37] Negishi [26] or Kumada [27] reactions with benzyl organometallics, aldol-type condensations, <...>…”

“…Most papers describing synthesis of (cyclo)alkylpiperidines according to the discussed strategy either relied on readily available alkyl-pyridines or did not focus on the preparation thereof. [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] Recent works which implied the strategy shown in Scheme 1 used the Sonogashira cross-coupling, [36,37] Negishi [26] or Kumada [27] reactions with benzyl organometallics, aldol-type condensations, [27,38] or reactions of lithiated pyridines with aromatic aldehydes, [39] carboxylic acids or their derivatives [40,41] to introduce the substituent at the pyridine ring prior the hydrogenation (Scheme 2). Therefore, these methods were limited in the substrate scope.…”