Efficient synthesis of organic thioacetates in water

• Published in: Organic & biomolecular chemistry Vol. 16; no. 41; pp. 7753 - 7759
• Main Authors: Olivito, F, Costanzo, P, Di Gioia, M. L, Nardi, M, Procopio, A
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 07.11.2018; Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Organic; Decomposition reactions; NMR; Nuclear magnetic resonance; Organosulfur compounds; pH control; Physical Sciences; Potassium carbonate; Science & Technology; Thiols; THIOLS; SOLVENT-FREE; AMINO-ACIDS; ALPHA; SULFUR; STEREOSELECTIVE-SYNTHESIS; CATALYST; POTASSIUM CARBONATE; S(N)2 REACTION; HIGHLY EFFICIENT
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/c8ob01896k

Thioacetates as precursors of thiols are interesting starting points for synthesizing other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention that has been paid toward environmentally friendly synthetic procedures in the past decades, we prove the role and the strength of the thioacetate anion as a nucleophile for nucleophilic displacement reactions in an aqueous medium. The reactions were carried out under pH control, to prevent the decomposition of the mesylate starting materials, using potassium carbonate as a safe and mild base. A simple work up allows products to be obtained with excellent yield and acceptable purity. A green, mild and safe synthetic procedure to obtain organic thioacetates in almost quantitative yield via aqueous nucleophilic displacement.