Diphenylsilylene Transfer to Unsymmetrical 1,3-Dienes: Synthesis of 2,3-Dihydrosiloles through Carbon Skeletal Reorganization
Abstract
The silylene transfer to 1,3-dienes with carbon skeletal reorganization is a powerful method for construction of silacarbocycles. However, the reaction of unsymmetrical 1,3-dienes posed the challenge of producing a mixture of two structural isomers. Herein, we demonstrate the diphenylsilylene transfer from Ph 2 (Et 2 N)Si–B(pin) to styrylcycloalkenes. This reaction selectively afforded one isomer of the possible 2,3-dihydrosiloles. We also report on a palladium-catalyzed 1,3-diene-silylene (4 + 1) cycloaddition to afford 2,5-dihydrosiloles from the identical starting materials.
Fields of Study & Subjects
Organoboron and organosilicon chemistry
Synthesis and characterization of novel inorganic/organometallic compounds
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 24
- Pages
- 7645–7650
- Publication date
- 8 June 2026
- Language
- EN