Tetrahedron

SmI 2/H 2 O/amine promoted reductive cleavage of benzyl-heteroatom bonds: optimization and mechanism

T Ankner, G Hilmersson

Index: Ankner, Tobias; Hilmersson, Goeran Tetrahedron, 2009 , vol. 65, # 52 p. 10856 - 10862

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Citation Number: 36

Abstract

The SmI2/H2O/pyrrolidine mediated cleavage of benzylic alcohols and benzyl groups was studied and found to be a viable alternative to the Birch reduction yielding the corresponding deoxygenated product in excellent yield. The reaction has been investigated by kinetic methods, and a mechanism involving a pre-complexation of the alcohol to SmI2 followed by an amine mediated electron transfer and subsequent bond cleavage and transfer of a ...