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Updated: Oct 1, 2025
![The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F54498.jpg&w=3840&q=50)
The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
Published on: November 28, 2016
Nickel-Catalyzed Reductive C(sp2 )-Si Coupling of Chlorohydrosilanes via Si-Cl Cleavage
Zhen-Zhen Zhao1, Xiaobo Pang1, Xiao-Xue Wei1
1State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, China.
Abstract:
We report here a new method for the synthesis of organohydrosilanes from phenols and ketones. This method is established through reductive C-Si coupling of chlorohydrosilanes via unconventional Si-Cl cleavage. The reaction offers access to aryl- and alkenylhydrosilanes with a scope that is complementary to those of the established methods. Electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles, as well as cyclic and acyclic alkenyl electrophiles, were coupled successfully. Functionalities, including Grignard-sensitive groups (e.g., primary amine, amide, phenol, ketone, ester, and free indole), acid-sensitive groups (e.g., ketal and THP protection), alkyl-Cl, pyridine, furan, thiophene, Ar-Bpin, and Ar-SiMe3 , were tolerated. Gram-scale reaction, incorporation of -Si(H)R2 into complex biologically active molecules, and derivatization of formed organohydrosilanes are demonstrated.
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