A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media

Abstract

A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.

Iodine-promoted decarboxylative C–S cross-coupling of cinnamic acids with sodium benzene sulfinates

“…6 Hz,1H),7H),7.73 (d,J = 15.2 Hz,1H),2H); 13 C NMR (100 MHz, CDCl 3 ) δ 123.6 (d, J = 270.0 Hz), 126.1 (q, J = 3.5 Hz), 127. 8,128.8,129.5,130.0,132.6 (q,J = 32.5.0 Hz),133.8,135.7,140.1,140.5; LRMS: m/z calcd for C 15 7.36 (d,J = 8.4 Hz,2H),7.43 (d,J = 8.8 Hz,2H),2H),2H),2H); 13 C NMR (100 MHz, CDCl 3 ) δ 127. 7, 127.9, 129.4, 129.4, 129.8, 130.9, 133.6, 137.2, 140.5, 141 5, 126.1, 127.6, 128.6, 129.3, 129.6, 129.8, 133.3, 140.9, 141.9, 142.6; LRMS: m/z calcd for C 15 125.3, 125.8, 126.6, 127.4, 127.8, 128.9, 129.4, 129.5, 129.6, 131.3, 131.5, 133.5, 133.7, 139.6, 140.6; LRMS: m/z calcd for C 18 4, 127.6, 128.4, 129.4, 130.1, 132.5, 133.4, 135.2, 136.9, 140.8 7, 114.6, 127.9, 128.5, 129.1, 129.9, 131.1, 132.2, 132.5, 141.4, 163.6; LRMS: m/z calcd for C 15 …”

“…Thus, the development of efficient synthetic methods about vinyl sulfones gains great attention. In the past several years, many methods for the synthesis of vinyl sulfones focused on palladium-or copper-catalyzed sulfonylation of alkynes 3 , olefins 4 , vinyl halides 5 , alkenyl boronic acids 6 , vinyl tosylates 7 or epoxides 8 . Although great efforts have been made, we thought it would be interesting to synthesize vinyl sulfones through some straight ways.…”

Regioselective, One‐Pot, Three‐Component Synthesis of 1,3,4‐ and 1,3,5‐Triarylpyrazoles from 1‐ and 2‐Aryl‐1‐alkenyl Sulfones

“…Another alkenyl sulfone, 10a, [45] was prepared by the nucleophilic substitution of 4-methylbenzyl chloride (8) with phenylsulfinate anion, followed by exo-methylene formation. A crucial, one-pot three-component coupling of aldehyde 11a, hydrazine 12b, and sulfonyl alkenes 7a and 10a was examined following the procedure reported by the Deng group (Scheme 3).…”

Recent advances in the synthesis of vinyl sulfones

“…66 Recently, using water as the reaction solvent, an efficient regioselective preparation of vinyl sulfones catalysed by Lithium bromide from sodium sulfinates and terminal epoxides in a one-pot procedure was disclosed by Yadav and co-workers. 67 Very recently, an efficient silver-catalyzed one-pot protocol for the highly stereoselective synthesis of (E)-vinyl sulfones by denitrative radical cross-coupling of readily available βnitrostyrenes and sodium sulfinates at room temperature under mild reaction conditions was investigated by Yadav and coworkers 69 (scheme 41). This is the first report on the facile formation of C(sp2)-S bonds leading to vinyl sulfones.…”