![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Palladium-catalyzed sequential three-component reactions to access vinylsilanes.
Bo Zhou1, Ailan Lu1, Changdong Shao1
1School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical, Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China. zhangyanghui@tongji.edu.cn.
Chemical Communications (Cambridge, England)
|September 4, 2018
Summary
A new palladium-catalyzed reaction creates vinylsilanes from aryl halides and alkynes. These vinylsilanes are versatile intermediates, readily converted into valuable tetrasubstituted alkenes.
Area of Science:
- Organic Chemistry
- Catalysis
- Organosilicon Chemistry
Background:
- Palladium catalysis is crucial for C-C bond formation.
- Vinylsilanes are important synthetic intermediates.
- Efficient synthesis of tetrasubstituted alkenes remains a challenge.
Purpose of the Study:
- To develop a novel palladium-catalyzed sequential three-component reaction.
- To synthesize vinylsilanes efficiently.
- To demonstrate the utility of vinylsilanes in preparing tetrasubstituted alkenes.
Main Methods:
- A sequential three-component reaction involving aryl halides, alkynes, and hexamethyldisilane.
- Palladium catalysis to generate key palladacycle intermediates.
- Cascade reaction mechanism.
Main Results:
- Successful synthesis of disilylated products via palladacycle intermediates.
- Demonstration of a useful preparative method for vinylsilanes.
- Transformation of vinylsilanes into tetrasubstituted alkenes.
Conclusions:
- A novel and efficient palladium-catalyzed route to vinylsilanes has been established.
- The developed method provides access to valuable tetrasubstituted alkenes.
- This reaction expands the synthetic utility of organosilicon compounds.
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