SYNTHESIS OF ARYZINC COMPOUNDS AND THEIR APPLICATIONS TO ORGANIC SYNTHESIS

芳基锌化合物的合成及其在有机合成中的应用

基本信息

  • 批准号:
    05640667
  • 负责人:
  • 金额:
    $ 1.28万
  • 依托单位:
  • 依托单位国家:
    日本
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)
  • 财政年份:
    1993
  • 资助国家:
    日本
  • 起止时间:
    1993 至 1994
  • 项目状态:
    已结题

项目摘要

Organozinc compounds continue to attract synthetic organic chemists to a great extent because if their high chemoselectivity and specific reactivity observed in their further transformations. In this research, we investigated for the first time the direct synthesis of arylzinc compounds from aryl halides and zinc powder promoted by the irradiation of ultrasound. In this method, arylzinc compounds containing electron-withdrawing groups at ortho-positions were obtained readily. The zinc compounds were converted into multi-functional biaryls, which are othewise very difficult to prepare, in high yields by their reaction with aryl halides in the presence of Pd (0)-catalysts.This activation method was also applied to the reaction of o-diiodobenzene with zinc powder, which resulted in the first formation of o-phenylenedizinc compound. After the treatment with chlorotrimethyltin, the zinc compound was identified as the known tin-compound of the corresponding structure. Then, the zinc compound was converted into symmetrical o-terphenyls or 1,2-diacylbenzenes in high yields by the reaction with aryl halides or acyl halides in the presence of Pd (0)-catalyst. Selective monoacylation was also accomplished by the same reaction with acyl halides, except for the use of tris-(2,4,6-trimethoxyphenyl) phosphine in place of other phosphorus ligands in Pd (0) complex.In these studies, we also found the novel displacement of metal ions from organozinc compounds with such nucleophilic reagents as halide ion, thiocyanate ion, or N,N-dialkyldi-thiocarbamate ions by the assistance of NCS.Whereby various organic N,N-dialkyldithio-carbamates or organic thiocyanates were obtained in high yields.
有机锌化合物在很大程度上吸引着合成有机化学家,因为它们具有高的化学选择性和特殊的反应活性。本研究首次探索了在超声作用下,芳基卤化物和锌粉直接合成芳基锌化合物的方法。在该方法中,容易地获得在邻位上含有吸电子基团的芳基锌化合物。在Pd(0)-催化剂存在下,锌化合物与卤代芳烃反应,高产率地转化为多官能联芳基化合物,并将此活化方法应用于邻二碘苯与锌粉的反应,首次生成邻苯二锌化合物。在用三甲基氯锡处理后,锌化合物被鉴定为相应结构的已知锡化合物。然后,在Pd(0)催化剂存在下,锌化合物与卤代芳烃或酰卤反应,高产率地转化为对称的邻三联苯或1,2-二酰基苯。选择性单酰化也通过与酰卤的相同反应来完成,除了使用三酰化的三酰化。在这些研究中,我们还发现了诸如卤素离子、硫氰酸根离子或N,N-二烷基二硫代氨基甲酸根离子,从而高产率地得到各种有机N,N-二烷基二硫代氨基甲酸酯或有机硫氰酸酯。

项目成果

期刊论文数量(16)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Kentaro Takagi: "Ortho-phenylenedizinc(II)Compounds.Ultrasound-Promoted Synthesis from 0-Diiodobenzene and Zink Powder and Its Synthetic Application" Chemistry Letters. 1994. 2055-2058 (1994)
Kentaro Takagi:“邻苯二甲酰(II)化合物。超声波促进 0-二碘苯和锌粉的合成及其合成应用”化学快报。
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  • 影响因子:
    0
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  • 通讯作者:
K.SASAKI, K.TAKAGI et al.: "Ni (0)-Triphenyl-phosphine Catalyzed Homo-Coupling of 1-Alkenyl Halides with Zinc Powder" Bulletin of the Chemical Society of Japan. 60. 2446-2448 (1993)
K.SASAKI、K.TAKAGI 等人:“Ni(0)-三苯基膦催化 1-烯基卤化物与锌粉的均相偶联”日本化学会通报。
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    0
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Kentaro Takagi: "Ultrasound-Promoted Synthesis of Arylzinc Compounds Using Zinc Powder and Their Application to Palladium(O)-Catalyzed Synthesis of Multifunctional Biaryls" Chemistry Letters. 1993. 469-472 (1993)
Kentaro Takagi:“超声促进使用锌粉合成芳基锌化合物及其在钯 (O) 催化合成多功能联芳基化合物中的应用”化学快报。
  • DOI:
  • 发表时间:
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  • 影响因子:
    0
  • 作者:
  • 通讯作者:
K.TAKAGI, et al.: "Ortho-phenylenedizinc (II) Compound. Ultrasound Promoted Synthesis from o-Diiodobenzene and Zinc Powder and Its Synthetic Application" Chemistry Letters. 1994. 2055-2058 (1994)
K.TAKAGI 等人:“邻苯二甲酰 (II) 化合物。超声促进邻二碘苯和锌粉的合成及其合成应用”化学快报。
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  • 发表时间:
  • 期刊:
  • 影响因子:
    0
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  • 通讯作者:
H.TSUKUBE, K.TAKAGI, et al.: "Biomimetic Membrance Transport : Interesting Ionophore Function of Naturally Occurring Polyether Antibiotics toward Unusaual Metal Cations and Amino Acid Ester Salts" Inorganic Chemistry. 33. 2694-2697 (1994)
H.TSUKUBE、K.TAKAGI 等人:“仿生膜传输:天然存在的聚醚抗生素对不寻常金属阳离子和氨基酸酯盐的有趣离子载体功能”无机化学。
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    0
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TAKAGI Kentaro其他文献

TAKAGI Kentaro的其他文献

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{{ truncateString('TAKAGI Kentaro', 18)}}的其他基金

Response of tree roots activity to atmospheric temperature through its trunk in deep winter snowpack
深冬积雪中树根活动通过树干对大气温度的响应
  • 批准号:
    16K14934
  • 财政年份:
    2016
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Challenging Exploratory Research
Large scale evaluation of decadal forest biomass changes using repeated airborne LiDAR observations in northern Japan
使用日本北部机载激光雷达重复观测对十年来森林生物量变化进行大规模评估
  • 批准号:
    26292076
  • 财政年份:
    2014
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Smart Vibration Suppression Using Generalized Virtual Impedance Circuit
使用广义虚拟阻抗电路的智能振动抑制
  • 批准号:
    23760204
  • 财政年份:
    2011
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Young Scientists (B)
Long-term evaluation of soil-warming effect on carbon and nitrogen dynamics of Japanese forest soils
土壤变暖对日本森林土壤碳氮动态影响的长期评估
  • 批准号:
    22310019
  • 财政年份:
    2010
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Distributed Parameter Systems Modeling and Bio-Mimetic Control of Artificial Muscle Polymer Actuators
人工肌肉聚合物致动器的分布式参数系统建模和仿生控制
  • 批准号:
    19760169
  • 财政年份:
    2007
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Young Scientists (B)
Synthesis of arylzinc compounds in ethereal solvent and application to organic synthesis
醚溶剂中芳基锌化合物的合成及其在有机合成中的应用
  • 批准号:
    13640592
  • 财政年份:
    2001
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Synthesis of o-Arylenedizinc Compounds and Their Synthetic Applications
邻亚芳基锌化合物的合成及其合成应用
  • 批准号:
    07640787
  • 财政年份:
    1995
  • 资助金额:
    $ 1.28万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
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