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Up-Scale Synthesis of p-ClC6H4SiR3 by CuCN Catalyzed Coupling Reaction of Grignard Reagents with R3SiCl
- Author(s)
- 고지형
- Advisor
- 이분열
- Department
- 일반대학원 분자과학기술학과
- Publisher
- The Graduate School, Ajou University
- Publication Year
- 2023-02
- Language
- eng
- Keyword
- CuCN catalyst; R3SiCl; p-ClC6H4SiR3
- Alternative Abstract
- 1-Octene is consumed as a comonomer in the polyethylene processes and its demand is increasing continuously. Herein, we propose the synthesis method of p-ClC6H4SiR3 using the Grignard reaction. But, sterically encumbered R3SiCl did not react with p-ClC6H4MgCl, necessitating the development of a catalyst for the coupling reaction of the Grignard reagent with such bulky R3SiCl. The reaction occurred with the addition of 3 mol% CuCN catalyst, affording the desired compound p-ClC6H4SiR3. The structure of p-ClC6H4MgCl was elucidated, which existed as an aggregate with MgCl2, indicating that some portion of the Grignard reagents were possibly lost in the coupling reaction due to co-precipitation with the byproduct MgCl2. Without formation of R4Si, R3SiCl could synthesized simply and economically when SiCl4 was reacted with 4 equiv of RMgCl. Using the developed syntheses, iPrN[P(C6H4-p-SiR3)2]2, which are potentially useful compounds for the production of 1-octene, was efficiently prepared with considerable reductions.
- Fulltext
- Appears in Collections:
- Graduate School of Ajou University > Department of Molecular Science and Technology > 3. Theses(Master)
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