Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: a simple and convenient approach to (E)-β-iodovinyl sulfones

Abstract

A simple and convenient approach for the construction of β-iodovinyl sulfones has been developed via direct difunctionalization of alkynes with sulfinic acids and molecular iodine.

Synthesis of Vinyl Sulfones through Visible Light‐Induced Decarboxylative Sulfonylation of Cinnamic Acids with Disulfides

“…The reaction vessel was irradiated under blue LED irradiation (450-455 nm, 3.0 W) in air at room temperature for 24 h. After completion of the reaction, the mixture was concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate) to give the desired product (E)-(2-(phenylsulfonyl)vinyl)benzene (3 a) in 75% yield. 13 13 C NMR (100 MHz, CDCl 3 ) δ: 142. 5, 141.8, 141.0, 133.2, 129.7, 129.6, 129.2, 128.5, 127.5, 126.1, 21.4;IR (KBr): 3053, 2918, 1604, 1510, 1446, 1306, 1143, 1082 13 C NMR (100 MHz, CDCl 3 ) δ: 152.…”

“…13 13 C NMR (100 MHz, CDCl 3 ) δ: 142. 5, 141.8, 141.0, 133.2, 129.7, 129.6, 129.2, 128.5, 127.5, 126.1, 21.4;IR (KBr): 3053, 2918, 1604, 1510, 1446, 1306, 1143, 1082 13 C NMR (100 MHz, CDCl 3 ) δ: 152. 6, 142.5, 140.9, 133.2, 129.9, 129.2, 128.6, 127.5, 127.1, 126.2, 34.0, 23.6;IR (KBr): 3058, 2919, 1606, 1309, 1155, 1146 13 C NMR (100 MHz, CDCl 3 ) δ: 143.…”

“…5, 141.8, 141.0, 133.2, 129.7, 129.6, 129.2, 128.5, 127.5, 126.1, 21.4;IR (KBr): 3053, 2918, 1604, 1510, 1446, 1306, 1143, 1082 13 C NMR (100 MHz, CDCl 3 ) δ: 152. 6, 142.5, 140.9, 133.2, 129.9, 129.2, 128.6, 127.5, 127.1, 126.2, 34.0, 23.6;IR (KBr): 3058, 2919, 1606, 1309, 1155, 1146 13 C NMR (100 MHz, CDCl 3 ) δ: 143. 8, 141.9, 140.7, 139.6, 133.2, 131.1, 129.2, 129.0, 128.8, 128.0, 127.5, 127.0, 126.9;IR (KBr): 3062, 2935, 1610, 1520, 1447, 1308, 1143, 1084 52 (m, 4H), 7.00-6.98 (m, 1H), 6.93 (s, 1H), 6.81-6.79 (m, 1H), 6.70-6.65 (m, 1H), 6.00 (s, 2H).…”

“…8, 141.9, 140.7, 139.6, 133.2, 131.1, 129.2, 129.0, 128.8, 128.0, 127.5, 127.0, 126.9;IR (KBr): 3062, 2935, 1610, 1520, 1447, 1308, 1143, 1084 52 (m, 4H), 7.00-6.98 (m, 1H), 6.93 (s, 1H), 6.81-6.79 (m, 1H), 6.70-6.65 (m, 1H), 6.00 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ: 150. 3, 148.4, 142.2, 141.0, 133.1, 129.2, 127.4, 126.6, 125.2, 125.0, 108.6, 106.8, 101.7;IR (KBr): 3053, 2904, 1595, 1500, 1488, 1447, 1307, 1257, 1139, 1082 3048, 1613, 1599, 1509, 1446, 1302, 1280, 1230, 1141, 1082 cm 140.5, 137.2, 133.5, 130.9, 129.7, 129.4, 128.0, 127.7;IR (KBr): 3054, 1741, 1614, 1445, 1307, 1146, 1083 cm À 1 ; HRMS (ESI) [M + Na] + : Calcd.…”

Recent advances in the synthesis of vinyl sulfones

“…DME, dimethylether. 29 also presented a protocol of direct difunctionalization of alkynes with arylsulfinic acids and molecular iodine for the preparing (E)-β-iodovinyl sulfones (Scheme 12). Without metal catalyst or additives, various substituted (E)-β-iodovinyl sulfones in moderate to good yields with excellent stereo-and regioselectivities were provided.…”