1. Nickel-Catalyzed Hydrosilylation of Terminal Alkenes with Primary Silanes via Electrophilic Silicon-Hydrogen Bond Activation
- Author
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Xiaomin Xie, Jingyang Wang, Guangni Ding, Zhaoguo Zhang, Wenkui Lu, Liqun Yang, Xiaoyu Wu, and Yuxuan Zhang
- Subjects
Silanes ,010405 organic chemistry ,Hydrogen bond ,Hydrosilylation ,Organic Chemistry ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Nickel ,chemistry ,Functional group ,Electrophile ,Physical and Theoretical Chemistry ,Selectivity - Abstract
We report a simple and effective nickel-based catalytic system, NiCl2·6H2O/tBuOK, for the electrophilically activated hydrosilylation of terminal alkenes with primary silanes. This protocol provides excellent performance under mild reaction conditions: exclusive anti-Markovnikov selectivity, broad functional group tolerance (36 examples), and good scalability (TON = 5500). However, the secondary and tertiary silanes are not suitable. Mechanistic studies revealed that this homogeneous catalytic hydrosilylation includes an electrophilically activated Si-H bond process without the generation of nickel hydrides.
- Published
- 2021