Direct radical sulfonylation at α-C(sp3)-H of THF with sodium sulfinates in aqueous medium. Issue 11 (14th March 2019)

• Record Type: Journal Article
• Authors: Singh, Manjula; Yadav, Lal Dhar S.; Singh, Rana Krishna Pal
• Is Part Of: Tetrahedron letters. Volume 60:Issue 11(2019)
• Page Start: 810
• Page End: 813
• Publication Date: 2019-03-14
• Subjects: Radical reaction -- Sodium sulfinates -- Sulfonylation -- THF derivatives; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.02.021
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Transition-metal-free one-pot approach to 2-alkyl/aryl THFs at rt. The direct radical sulfonylation at α-C(sp 3 )-H of THF in aqueous medium. Sodium sulfinates as a radical source. K2 S2 O8 as a mild radical initiator. Abstract: A direct transition-metal-free, convenient and highly regioselective synthesis of 2-alkyl/aryl sulfonyl tetrahydrofurans (THFs) has been achieved from THF and sodium sulfinates using K2 S2 O8 as a mild oxidant. This one-pot simple protocol involves an efficient radical cross coupling reaction in aqueous medium utilizing K2 S2 O8 as an inexpensive and easy to handle radical surrogate at room temperature.