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Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

Tanja Stach, Julia Dräger and Peter H. Huy*

*Institute of Organic Chemistry, Saarland University, P.O. Box 151150, D-66041 Saarbruecken, Germany, Email: peter.huyuni-saarland.de

T. Stach, J. Dräger, P. H. Huy, Org. Lett., 2018, 20, 2980-2983.

DOI: 10.1021/acs.orglett.8b01023 (free Supporting Information)


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Abstract

A practical nucleophilic substitution of alcohols furnishes alkyl chlorides, bromides, and iodides under stereochemical inversion in the presence of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent. Moreover, acetyl chloride has been used as a stoichiometric promotor in an invertive SN-type transformation for the first time.

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Key Words

alkyl chlorides, benzyl chlorides, organocatalysis


ID: J54-Y2018