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1.3.1.1 Ruthenium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkanes

DOI: 10.1055/sos-SD-226-00066

Dai, X.; Shi, F.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20171128.

Benzene and a large number of mono-, di-, and tri-substituted derivatives (e.g., 1 and 3) can be reduced to give the corresponding cyclohexane derivatives (e.g., 2 and 4) in good to excellent results using the ruthenium-based catalysts Ru2Cl46-C6H6)2 (Scheme 2)[‌29‌] or ruthenium nanoparticles stabilized by hyperbranched polystyrene (HPS) bearing ammonium salts [Ru@HPS-N+Bu3Cl] (Scheme 3).[‌30‌] Benzene and electron-rich analogues give excellent yields, whereas more electron-deficient arenes [e.g., benzoic acid (1, R1 = CO2H; R2 = R3 = R4 = R5 = H)] result in lower yields with catalyst Ru2Cl46-C6H6)2. The hyperbranched-polystyrene-stabilized ruthenium catalyst has no activity in the case of starting materials with strong electron-withdrawing groups (e.g., 3, R1 = NO2). Both ruthenium-based catalysts show poor tolerance of other reducible functional groups.

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