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Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling

Lars Longwitz, Stefan Jopp, Thomas Werner*

*Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Straße 29a, 18059 Rostock, Germany, Email: thomas.wernercatalysis.de

L. Longwitz, S. Jopp, T. Werner, J. Org. Chem., 2019, 84, 7863-7870.

DOI: 10.1021/acs.joc.9b00741 (free Supporting Information)


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Abstract

In a catalytic system for the chlorination of alcohols under Appel conditions, benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant under solvent-free conditions. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in good yields.

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proposed mechanism



Key Words

Appel reaction, organocatalysis, benzyl chlorides, alkyl chlorides, phenylsilane


ID: J42-Y2019