Palladium-Catalyzed (Asymmetric) B(9)-Alkylation of o / m -Carboranes with α-Aryl-α-diazoesters
Abstract
Although Pd(II)-catalyzed selective B(9)–H activation of o / m -carboranes via an electrophilic palladation process has been well explored, other pathways in directly Pd(II)-catalyzed B(9)–H functionalization have not been reported. Herein, we report an efficient Pd(II)-catalyzed selective B(9)–H alkylation of o / m -carboranes via a carbene B–H insertion process, in which α-aryl-α-diazoesters serve as carbene precursors. The reaction features good B(9) selectivity, mild reaction conditions without any additives, and a broad substrate scope. Furthermore, an asymmetric version was explored by adding a chiral phosphoric acid to the reaction system, and up to 88% ee was obtained.
Fields of Study & Subjects
Boron Compounds in Chemistry
Cyclopropane Reaction Mechanisms
Organoboron and organosilicon chemistry
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 21
- Pages
- 6521–6527
- Publication date
- 15 May 2026
- Language
- EN