Rhodium-Catalyzed Formal C–H and X–H Insertion Reaction Involving an Exocyclic Vinylic Cation Intermediate
Abstract
The carbocation is one of the highly reactive intermediates in synthetic chemistry; however, catalytic selective transformations involving vinylic cation species remain elusive in comparison to sp 2 -hybrid ones. Herein, we report a Rh-catalyzed formal C–H and X–H insertion reaction of in situ-generated exocyclic vinylic cations with a variety of nucleophiles, affording tetrasubstituted alkenes incorporating a cyclobutanone motif with a broad substrate scope under mild conditions. The utility of this method has been demonstrated for the synthesis of 3-methylenecyclobutanone derivatives, which are difficult to access using other methods, serving as versatile building blocks for a range of postfunctionalization conversions.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Cyclopropane Reaction Mechanisms
Chemical Reactions and Isotopes
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 7
- Pages
- 2300–2305
- Publication date
- 4 February 2026
- Language
- EN