Catalytic C-C Bond Forming Reactions
Silaborative C-C Coupling Reaction
Silylboranes, 1,3-dienes, and aldehydes are coupled in the presence of a platinum catalyst [Ref. 1]. The reaction provided O-silylated homoallylic alcohols with high stereoselectivities for the syn-stereoisomers. The three-component coupling may involve σ-allylplatinum species as a key reactive interemediate.
Catalytic Hydroalkynylation
The C-H bonds of terminal alkynes are known to add not only to alkynes (homo- and cross-dimerization), but also to highly reactive C=C bonds in allenes, cyclopropenes, and norbornadiene. However, no reaction systems have been established for hydroalkynylation of less reactive C=C bonds. We found that the alkyne C–H bond adds to a carbon-carbon double bond of 1,3-dienes, styrenes, and norbornene at room temperature in the presence of a nickel catalyst in regio- and stereoselective manners [Ref. 2].
Related Researches
- Intramolecular Cyanoboration
- Cyanoboration
- Alkynylboration
- Transmetallative Cyclizative Carboboration
- Transmetallative Three-Component Carboboration
- Module-Based Iterative Cross-Coupling
- Asymmetric Polymerization
References
- Ref. 1
- Platinum-Catalyzed Silaborative Coupling of 1,3-Dienes to Aldehydes: Regio- and Stereoselective Allylation with Dienes through Allylic Platinum Intermediates M. Suginome, H. Nakamura, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 1998, 120, 4248-4249, 10.1021/ja980373o
- Ref. 2
- Nickel-Catalyzed Addition of C-H Bonds of Terminal Alkynes to 1,3-Dienes and Styrenes M. Shirakura, M. Suginome, J. Am. Chem. Soc. 2008, 130, 5410-5411, 10.1021/ja800997j