An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation. Issue 31 (2nd August 2019)

• Record Type: Journal Article
• Authors: Zuo, Yingying; Xiong, Feng; Zhao, Jing
• Is Part Of: Tetrahedron. Volume 75:Issue 31(2019)
• Page Start: 4174
• Page End: 4179
• Publication Date: 2019-08-02
• Subjects: Sulfenylation reagents -- Metal free -- Sulfilimines -- Internal oxidant -- Cascade reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.05.021
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C–S bond-forming methods. However, a mild, transition-metal-free, direct C–H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions. Graphical abstract: Image 1