Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 17, Pages 2999-3005Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600366
Keywords
Synthetic methods; Solid-state reactions; Sulfur; Zinc; Density functional calculations
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Funding
- Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Perugia (Fondo per il sostegno della Ricerca di Base)
- Fondazione Cassa di Risparmio di Perugia
- Regione Umbria, Italy
- CAPES [BEX 6391/14-1]
- Dipartimento di Scienze Chimiche e Geologiche of the Universita degli Studi di Cagliari
- Banco di Sardegna, Italy (PRID)
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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.
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