Heterogeneous reductive isomerization reaction using catalytic Pd/C and H2.

Org Lett

The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Published: June 2005

[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.

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http://dx.doi.org/10.1021/ol050952fDOI Listing

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