Cobalt-Promoted Photoredox 1,2-Amidoamination of Alkenes with N-Sulfonamidopyridin-1-ium Salts and Free Amines

Liang-Feng Yang; Zhi-Qiang Xiong; Xuan-Hui Ouyang; Qiu-An Wang; Jin-Heng Li

doi:10.1021/acs.orglett.4c00155

Cobalt-Promoted Photoredox 1,2-Amidoamination of Alkenes with N-Sulfonamidopyridin-1-ium Salts and Free Amines

Org Lett. 2024 Mar 1;26(8):1667-1671. doi: 10.1021/acs.orglett.4c00155. Epub 2024 Feb 21.

Authors

Liang-Feng Yang^{1

2}, Zhi-Qiang Xiong¹, Xuan-Hui Ouyang¹, Qiu-An Wang², Jin-Heng Li^{1

2

3

4}

Affiliations

¹ Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
² State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.
³ State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
⁴ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

PMID: 38380904
DOI: 10.1021/acs.orglett.4c00155

Abstract

A cobalt-promoted photoredox 1,2-amidoamination of alkenes with N-sulfonamidopyridin-1-ium salts and free amines for the synthesis of unsymmetrical vicinal diamines has been developed. The reaction handles N-(sulfonamido)pyridin-1-ium salts as the sulfonamidyl radical precursors and free amines as the nucleophilic terminating reagents to enable the formation of two new C(sp³)-N bonds in a single reaction step and offers a route to selectively producing unsymmetrical vicinal diamines with an exquisite selectivity and a good compatibility of functional groups.