Rhodium-catalyzed hydrogenation

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Rhodium catalyzed hydrogenation is a chemical reaction that typically involves the addition of pairs of hydrogen atoms to another compound or element in the presence of a Rhodium complex catalyst. The addition of hydrogen to double or triple bonds in hydrocarbons is a type of redox reaction that can be thermodynamically favorable without a catalyst.

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  • Characteristic features of this Rh-catalyst include (1) hydrogenation of double bonds via syn-addition of H2, (2) cis-double bonds are hydrogenated faster than trans-double bonds, (3) terminal double bonds are hydrogenated more rapidly than more substituted double bonds, (4) less isomerization of double bonds, (5) little hydrogenolysis of allylic or benzylic ethers and amines, and (6) R-C≡N, R-NO2, R-Cl, RCOOH, RCOOR', and R2C=O are not reduced.
    • George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 5 : Functional Group Transformations: The Chemistry of Carbon-Carbon π-Bonds and Related Reactions

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