K2S2O8-mediated decarboxylative oxysulfonylation of cinnamic acids: A transition-metal-free synthesis of β-keto sulfones. Issue 34 (22nd August 2019)

• Record Type: Journal Article
• Authors: Chawla, Ruchi; Kapoor, Ritu; Yadav, Lal Dhar S.
• Is Part Of: Tetrahedron letters. Volume 60:Issue 34(2019)
• Publication Date: 2019-08-22
• Subjects: Cinnamic acids -- Decarboxylative -- β-Keto sulfones -- Aerobic oxidation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.150964
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Metal-free one-pot approach to β-keto sulfones. Use of air and K2 S2 O8 as eco-friendly and inexpensive oxidants. Decarboxylative oxysulfonylation of cinnamic acids. A synthetically useful radical pathway is developed. Abstract: A new paradigm of the oxidative decarboxylative sulfono functionalization of cinnamic acids with sulfinate salts mediated by K2 S2 O8 under aerobic conditions to afford synthetically and biologically relevant β-keto sulfones has been described. It is the first report on the transition-metal-free synthesis of β-keto sulfones from cinnamic acids, which employs environmentally benign, readily available and inexpensive starting materials and oxidants, viz. air and K2 S2 O8 .