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Citation: XIA Yong-Tao, HE Ren, WANG Ji-Hua, SONG You-Yong, ZHOU Yin-Bo, CUI Ming. Suzuki Coupling Reaction Catalyzed by Pd(Ph₂PCH₂COO)₂ for Synthesis of Biaryl Type Liquid Crystal Containing Fluorine[J]. Chinese Journal of Applied Chemistry, ;2007, 24(5): 489-493. shu

Suzuki Coupling Reaction Catalyzed by Pd(Ph₂PCH₂COO)₂ for Synthesis of Biaryl Type Liquid Crystal Containing Fluorine

XIA Yong-Tao ^a,b ,
HE Ren ^a,, ,
WANG Ji-Hua ^b ,
SONG You-Yong ^b ,
ZHOU Yin-Bo ^b ,
CUI Ming ^b

1.
a Dalian University of Technology, State Key Laboratory of Fine Chemicals, Dalian 116012;
2.
b Yantai Valiant Fine Chemicals Co., Ltd, Yantai

Corresponding author: HE Ren,
Received Date: 5 July 2006
Available Online: 25 October 2006
Fund Project: 国家自然科学基金资助项目(20333060) (20333060)

4-[Trans-4'-(trans-4"-n-alkylcyclohexyl) cyclohexyl]bromobenzene (5) was synthesized with trans-4-(4'-n-alkylcyclohexyl) cyclohexanone and bromobenzene as the starting materials via Grignard reaction,dehydroxylation,catalytic hydrogenation,configuration translation and bromination.Six biaryl type liquid crystal compounds containing fluorine were synthesized by Suzuki coupling reaction between compound 5 and phenylboronic acid containing fluorine catalyzed by Pd(Ph₂PCH₂COO)₂.The total yields of the six biaryl type liquid crystal compounds containing fluorine after purification based on trans-4-(4'-n-alkylcyclohexyl) cyclohexanone were all ca.50%.In the process of synthesizing 4-(trans-4'-n-alkylcyclohexyl) cyclohexyl bezene,the cyclohexane intermediate was isomerized in DMF-t-Buok medium with the yield of 82%,much higher than expected (50%).The catalytic mechanism of the cis-trans cyclohexyl isomerization was discussed.The data of GC-MS and ¹H NMR proved that the target compounds were obtained indeed.The results of DSC show that these liquid crystal compounds exhibit a broad temperature range of mesomorphic phases and high clear points.
- liquid crystal compound,
- Suzuki coupling reaction,
- Pd(Ph₂PCH₂COO)₂,
- coordination (homogeneous) catalysis
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Suzuki Coupling Reaction Catalyzed by Pd(Ph₂PCH₂COO)₂ for Synthesis of Biaryl Type Liquid Crystal Containing Fluorine