One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita–Baylis–Hillman reaction as a key step. (3rd March 2016)

• Record Type: Journal Article
• Authors: Yang, Hae-Won; Choi, Ji-Su; Lee, Sang-Jin; Yoo, Byung-Woo; Yoon, Cheol Min
• Is Part Of: Journal of sulfur chemistry. Volume 37:Number 2(2016)
• Page Start: 134
• Page End: 140
• Publication Date: 2016-03-03
• Subjects: One-pot reaction -- benzaldehyde -- activated alkene -- Morita–Baylis–Hillman reaction -- allyl thioacetate; Sulfur -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.72305
• DOI: 10.1080/17415993.2015.1124275
• Languages: English
• ISSNs: 1741-5993

Abstract

Abstract : An efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of ( Z )- S -2-alkoxycarbonyl-3-acylallyl ethanethioates and ( E )- S -2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonitrile) was developed. Our method consisted of Morita–Baylis–Hillman reaction of benzaldehydes and activated alkenes using DABCO followed by acetylation using acetic anhydride and a catalytic amount of DMAP, and SN 2′ reaction with potassium thioacetate in DMF. The first two reactions proceeded under solvent-free condition. GRAPHICAL ABSTRACT: