Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

Abstract

Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.

Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

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Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

“…Quinolinyl ketones are regarded as a versatile directing group by the cooperation of transition metal catalysts for activating the organic transformation [77][78][79][80][81][82]. A variety of 2-aminobenzophenone 4 were subjected to react with propionaldehyde 2a in the optimized reaction condition.…”

Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes

“…The product was obtained as a white solid (706 mg, 54% yield) following silica gel column chromatography with hexanes/EtOAc (98/2). The spectroscopic data were in accordance with those previously published in the literature: 1 H NMR (400 MHz, CDCl 3 ) δ 7.61 (d, J = 15.5 Hz, 1H), 7.53 (d, J = 5.5 Hz, 2H), 7.46–7.43 (m, 3H), 6.81 (d, J = 15.5 Hz, 1H), 3.10 (q, J = 7.4 Hz, 2H), 1.39 (t, J = 7.4 Hz, 3H).…”