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2.5.1.1.5 Hydrogenation of Esters with Manganese Catalysts

DOI: 10.1055/sos-SD-227-00090

Shi, Y.; Cole-Hamilton, D. J.; Kamer, P. C. J.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20182208.

The first manganese catalyst for ester hydrogenation was reported by Beller in 2016.[‌56‌] Complexes 47 and 48 have the same activity for ester hydrogenation. Esters 51 with both electron-donating and electron-withdrawing groups can be hydrogenated to the corresponding alcohols 52 in moderate to good yields (Scheme 24, entries 3, 5, and 6). For the hydrogenation of methyl cyclohex-3-ene-1-carboxylate (Scheme 24, entry 8) and methyl oleate (Scheme 24, entry 23), the double bond remains intact. However, hydrogenation of conjugated methyl cinnamate (Scheme 24, entry 9) gives the saturated alcohol under these conditions. Lactones (Scheme 24, entries 11 and 12) and diesters (Scheme 24, entries 13 and 14) can also be converted into the corresponding diols in excellent yields.

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