Heterogeneous reductive isomerization reaction using catalytic Pd/C and H2.
[reaction: see text] A highly selective catalytic reductive isomerization reaction is described. The extremely mild and neutral reaction conditions (10% Pd/C, H2, and MeOH at 0 degrees C) tolerate a wide range of functional groups and generally result in excellent yields. Mechanistic studies suggest that this reaction does not proceed via a stepwise reduction/elimination sequence or a pi-allylpalladium intermediate.
Caspi
Daniel D
DD
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Garg
Neil K
NK
Stoltz
Brian M
BM
D002384:Catalysis; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007536:Isomerism; D000432:Methanol / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*
D006572:Heterocyclic Compounds, Bridged-Ring; D010636:Phenols; D011758:Pyrroles; D010165:Palladium; D006859:Hydrogen; D000432:Methanol