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- Title
Synthesis of Thiol Esters Using PhSZnBr as Sulfenylating Agent: A DFT-Guided Optimization of Reaction Conditions.
- Authors
Sancineto, Luca; Tidei, Caterina; Bagnoli, Luana; Marini, Francesca; Lippolis, Vito; Arca, Massimiliano; Lenardão, Eder João; Santi, Claudio
- Abstract
The use of PhSZnBr as sulfenylating agent in a solvent-free protocol to prepare thiol esters in excellent yields from acyl chlorides is reported. The products were efficiently obtained by grinding the neat reagents for 5 min in a mortar. DFT calculations showed that the coordination of solvent molecules to the metal center of PhSZnBr results in the destabilization of the frontier MOs, thus reducing the reactivity towards the acyl chloride compared with solvent-free conditions. A possible mechanism based on the coordination of the carbonyl group of the acyl chloride to the metal center of PhSZnBr is proposed.
- Subjects
THIOLS; THIOL synthesis; CHEMICAL reactions; ACYL chlorides; ORGANIC chemistry research
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 17, p2999
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600366