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Organocatalytic Stereospecific Appel Reaction
Jan Tönjes1, Lukas Kell1, Thomas Werner1,2
1Leibniz Institute for Catalysis at the University of Rostock (LIKAT Rostock), Albert-Einstein-Str. 29a, 18059 Rostock, Germany.
Abstract:
Herein we report a new method for the catalytic Appel reaction by P(III)/P(V) redox cycling at very low catalyst loadings of 1-2 mol % using low amounts of hexachloroacetone as the halogen source and phenylsilane as the terminal reductant. Twenty-six alcohols and nine epoxides containing a wide variety of functional groups were converted to the respective chlorides and dichlorides in yields of up to 97%, enantiospecificities of up to >99%, and enantiomeric ratios of up to >99:1.
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