Organophotoredox-Catalyzed Sulfurization of Alkenes and Alkynes: Selective and Controlled Synthesis of Sulfoxides, β-Hydroxysulfoxides, and β-Keto Sulfides

Rajjakfur Rahaman, Md Tanjul Hoque and Dilip K. Maiti*

*Department of Chemistry, University of Calcutta, 92 A. P. C. Road, Kolkata 700009, India, Email: dkmchemcaluniv.ac.in

R. Rahaman, M. T. Hoque, D. K. Maiti, Org. Lett., 2022, 24, 6885-6890.

DOI: 10.1021/acs.orglett.2c02307

---

see article for more reactions

Abstract

A visible light mediated sulfurization of alkenes and alkynes with aromatic and heteroaromatic thiols enables a benign and metal-free functionalization using Eosin Y as photocatalyst and eco-friendly air (O₂) as the sole oxidant. This selective approach shows good substrate generality to afford sulfoxides, β-hydroxysulfoxides, and β-keto sulfides in high yield.

see article for more examples

proposed mechanism

---

---

Key Words

sulfoxides, oxygen, organocatalysis, photochemistry

---

ID: J54-Y2022