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Thiourea-Mediated Halogenation of Alcohols

Amar R. Mohite, Ravindra S. Phatake, Pooja Dubey, Mohamed Agbaria, Alexander I. Shames, N. Gabriel Lemcoff* and Ofer Reany*

*Ben-Gurion University of the Negev, Beer-Sheva 8410501; The Open University of Israel, Ra'anana 4353701, Israel, Email: lemcoffbgu.ac.il, oferreopenu.ac.il

A. R. Mohite, R. S. Phatake, P. Dubey, M. Agbaria, A. I. Shames, N. G. Lemcoff, O. Reany, J. Org. Chem., 2020, 85, 12901-12911.

DOI: 10.1021/acs.joc.0c01431 (free Supporting Information)


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Abstract

Substoichiometric amounts of thiourea additives mediate the halogenation of alcohols under mild conditions. In the the absence of thiourea, oxidation of the alcohol is observed, whereas the substrate can be recovered when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups.


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Key Words

alkyl bromides, alkyl chlorides, benzyl bromides, benzyl chlorides, NBS, NCS, photochemistry


ID: J42-Y2020