Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates. Issue 38 (17th September 2020)

• Record Type: Journal Article
• Authors: Huang, Youming; Chen, Hongyi; Zheng, Wenting; Zeng, Qingle
• Is Part Of: Tetrahedron letters. Volume 61:Issue 38(2020)
• Publication Date: 2020-09-17
• Subjects: Copper(I) oxide -- Quaternary ammonium salts -- Sodium sulfinates -- Chiral sulfones -- C–S coupling; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152320
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new protocol to synthesize (enantioenriched) benzylic sulfones. Cu2 O as a heterogeneous catalyst can be recycled. The product benzylic sulfones were obtained in good to high yield (75 ~ 96%). Highly enantioenriched benzylic sulfones (90 ~ 95%ee) can be synthesized when dppf is used as a ligand. Abstract: A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2 O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2 O and 1, 1′-bis-(diphenylphosphino)ferrocene (dppf).