Transition Metal-Promoted Direct C-S and C-Se Bond Formation from Csp³-H Bonds

Author(s)

Paixao, Douglas B. ; Seckler, Diego ; Gomes, Carla M. B. ; Badshah, Gul ; Bueno, Gabriel P. ; Schneider, Paulo H. ; Schwab, Ricardo S. ; Rampon, Daniel S.

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 28, n. 20, p. 27-pg., 2025-05-02.

Abstract

The transition metal-catalyzed direct C-S and C-Se bond formation from C-H bonds has emerged as an efficient synthetic strategy for constructing previously inaccessible organochalcogen compounds, opening a new gateway to late-stage functionalization of pharmaceutical-relevant molecules and organic functional materials. C-Y bonds (Y=S, Se, Te) also show outstanding strategic relevance as handles to access other valuable functional groups downstream in a synthetic route. Despite the significant progress, the chemo-, site-, and enantioselective C-S and C-Se bond formation from unactivated Csp(3)-H bonds is still challenging owing to its low polarity and inertness. Here, a comprehensive overview of the transition metal-catalyzed direct conversion of unactivated Csp(3)-H to C-S and C-Se bonds in the last decade is provided, looking to motivate the continuous discovery of innovative and efficient systems for these transformations. (AU)

• FAPESP's process: 21/12394-0 - Sustainable synthetic methods employing catalysis, benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 13/06558-3 - Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants