Thiourea-Mediated Halogenation of Alcohols

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

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery 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. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

Original languageEnglish
Pages (from-to)12901-12911
Number of pages11
JournalJournal of Organic Chemistry
Volume85
Issue number20
DOIs
StatePublished - 16 Oct 2020

ASJC Scopus subject areas

  • Organic Chemistry

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