B(C 6 F 5 ) 3 -Catalyzed Intramolecular Thio- and Selenoamination of Aminoalkenes
Abstract
A metal-free borane-catalyzed chalcogenative cyclization strategy for constructing chalcogen-containing heterocycles from unactivated alkenes with thiosuccinimides or selenophthalimide is developed herein. This method results in excellent substrate and functional group tolerance and high levels of chemo- and regioselectivity. Furthermore, the protocol enables the late-stage diversification of commercially available pharmaceuticals. Mechanistic studies suggest that the borane catalyst activates thiosuccinimides and selenophthalimides to form electrophilic species, which subsequently induce this chalcogenative annulation.
Fields of Study & Subjects
Organoboron and organosilicon chemistry
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 4
- Pages
- 1670–1685
- Publication date
- 15 January 2026
- Language
- EN