Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation.

LV, GUANG-SHU; DUAN, FU-JUN; DING, JIN-CHANG; CHENG, TIAN-XING; GAO, WEN-XIA; CHEN, JIU-XI; WU, HUA-YUE

Rongalite® promotes cleavage of diaryl disulphides generating the corresponding thiolate species in situ which then undergo facile ring-opening of epoxides in a regioselective manner under ultrasound irradiation, affording β-hydroxy sulphides in good to excellent yields. The important features of this methodology are base-free, odourless, high yield, reasonably rapid reaction rate, simple workup, high regioselectivity, cost-effective and no requirement of transition metal catalysts. It is noteworthy that ring-opening reaction of 1,2-diphenyldiselane with 2-(phenoxymethyl)oxirane are also conducted smoothly to afford β-hydroxy selenide in excellent yield under the standard conditions. [Figure not available: see fulltext.]

HYDROXY acids; SULFIDES; THIOLATES; TRANSITION metal catalysts; CHEMICAL reactions; ETHYLENE oxide

Journal of Chemical Sciences, 2012, Vol 124, Issue 5, p1057

0974-3626

Academic Journal

10.1007/s12039-012-0305-6