Stock solution of SO₂ as practical reagent for Ni-electrocatalytic sulfinylation

Abstract

Sulfinates are important portals to various sulfonyl functional groups with wide applications and great societal impacts. The efficient synthesis of these versatile intermediates remains a key research topic in organosulfur chemistry. By employing Ni-electrocatalysis and SO₂ as the sulfur source, our recent work on the room-temperature sulfinylation of a broad scope of readily available aryl iodides and electron-deficient bromides is presented. With the scalability of the e-sulfinylation demonstrated in both batch and flow settings, the practical use of SO₂ stock solution is highlighted, and the preparation and titration of SO₂ stock solution are detailed.

GRAPHICAL ABSTRACT

Keywords:

• Electrochemistry
• nickel
• catalysis
• sulfinylation
• fluoride
• sulfur dioxide

Acknowledgments

The author would like to thank my current and former supervisors (Prof. Phil S. Baran and Prof. Michael C. Willis) for their guidance and support, as well as the Croucher Foundation for sponsoring my fellowship and the expenses for attending the conference. The author is also grateful to Prof. Adrian Schwan and the organizing committee for setting up the enjoyable ISOCS-29 meeting in Guelph.