引用本文:
夏永涛, 何仁, 王继华, 宋有永, 周银波, 崔明. 二苯基膦乙酸钯催化Suzuki偶联反应合成联苯类含氟液晶[J]. 应用化学,
2007, 24(5): 489-493.
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.
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.
二苯基膦乙酸钯催化Suzuki偶联反应合成联苯类含氟液晶
摘要:
以4-(反-4'-正烷基环己基)环己酮和溴苯为起始原料经格氏反应、脱水、催化氢化、构象转化、溴代,合成了4-[反-4-'(反-4"-正烷基环己基)-环己基]溴苯(5)。在二苯基膦乙酸钯催化下由化合物5与含氟苯硼酸偶联,合成了6个联苯类含氟液晶化合物。以4-(反-4'-正烷基环己基)环己酮计,纯化处理后的总收率约50%。采用了DMF、叔丁醇钾体系,实现了环己烷顺、反异构体构型转换,使得反式-4-(反式-4'-正烷基环己基)-环己基苯(4)的收率达到82%,并对环己烷构型转换可能的机理进行了探讨。目标化合物经GC-MS、1H NMR测试技术表征,证明得到了预期的结果。DSC分析表明,该类液晶化合物有很高的清亮点和较宽的介晶相变温度。
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关键词:
- 液晶化合物
- / Suzuki偶联反应
- / 二苯基膦乙酸钯
- / 配位催化
English
Suzuki Coupling Reaction Catalyzed by Pd(Ph2PCH2COO)2 for Synthesis of Biaryl Type Liquid Crystal Containing Fluorine
Abstract:
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.
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