Synthesis of Advanced Organic Materials with CH Substitution Reactions of Heteroaromatic Compounds

杂芳族化合物CH取代反应合成先进有机材料

• 批准号: 16550092
• 负责人: MORI Atsunori
• 金额: $ 2.5万
• 依托单位: Kobe University (2005)Tokyo Institute of Technology (2004)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2004
• 资助国家: 日本
• 起止时间: 2004 至 2005
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-16550092/
• 关键词: thiazole; thiophene; palladium catalyst; silver nitrate; potassium fluoride; intramolecular CH substitution; condensed nitrogen heterocycles; alkyne spacer; oligothiophene; 2,5-ジアリールチアゾール; パラジウム; フッ化銀; 2,5-ジアリールチオフェン; ホモカップリング; C-H結合; プロモチオ

C-H substitution reaction at the 5-position of thiophene was revealed to proceed with silver (I) nitrate and potassium fluoride as an activator. Addition of the activator in 2-5 portions drastically improved the yield of the coupling product.Cyclization precursors of intramolecular CH substitution reactions of nitrogen heteroaromatic compounds such as imidazoles and pyrroles were designed. The cyclization reaction enabled the formation of fused nitrogen heterocycles of complicated structre in a facile manner.In the combination of CH substitution reaction of heteroaromatic compound with coupling reaction of terminal alkynes with novel activators, which we developed recently, allowed the formation of 2, 5-diarylthiophenes and 2, 5-diarylthiazoles with alkyne spacer. Changes of spectroscopic properties of the produced compounds were discussed.With continueous homocoupling of thiophenes at the CH bond as a key reaction, well-defined oligothiophenes bearing 2-8 thiphene units were synthesized. Since the produced oligothiophenes possess carbon-bromine bond at the end thiophene ring, further modification with several functional groups were made possible. A transition metal-catalyzed coupling reaction furnished further functionalized oligothiophenes.

硫苯5位的C-H取代反应揭示了以银（I）硝酸盐和氟钾作为激活剂进行的。在2-5个部分中添加激活剂可大大提高耦合产物的产量。设计了氮异质化合物（例如咪唑和吡格唑）和吡格唑等氮内CH取代反应的环化前体。环化反应使复杂的结核的融合氮异构体形成。在终末碱与新活化剂的偶联反应与新型激活剂的偶联反应的结合中，我们最近开发了2、5-二叶thiphiophenes and 2 iarylkylkylkylkylkylkylkylkylkysiaze space spass允许形成。讨论了产生化合物的光谱特性的变化。硫代在CH键处的持续同耦合作为关键反应，合成了2-8个噻吩单元的定义明确的寡硫醇。由于产生的寡硫苯在末端硫芬环处具有碳 - 溴键，因此通过几个官能团进行了进一步的修饰。过渡金属催化的耦合反应提供了进一步的寡头碘。

项目成果

Comprehensive Organometallic Chemistry 3

综合有机金属化学3

• 发表时间: 2006
• 作者: Mohamed S.Mohamed Ahmed;Mohamed S.Mohamed Ahmed;Mohamed S.Mohamed Ahmed;Atsunori Mori;M.S.Mohamed Ahmed;M.S.Mohamed Ahmed;K.Masui;K.Masui;森 敦紀;T.Sanada;A.Mori
• 通讯作者: A.Mori

複素環化合物の製造方法、および触媒系

杂环化合物的制造方法及催化剂体系

• 发表时间: 2004

Palladium-catalyzed C-H homocoupling ot thiophenes : Facile construction of bithiophene structure

钯催化的噻吩 C-H 自偶联：联噻吩结构的简便构建

• 发表时间: 2004
• 期刊: J.Am.Chem.Soc. 126・16
• 作者: Mohamed S.Mohamed Ahmed;Mohamed S.Mohamed Ahmed;Mohamed S.Mohamed Ahmed;Atsunori Mori;M.S.Mohamed Ahmed;M.S.Mohamed Ahmed;K.Masui
• 通讯作者: K.Masui

One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling

• DOI: 10.1021/ol051841j
• 发表时间: 2005-09-29
• 期刊: ORGANIC LETTERS
• 影响因子: 5.2
• 作者: Ahmed, MSM;Kobayashi, K;Mori, A
• 通讯作者: Mori, A

Cross-Coupling Polymerization

• DOI: 10.1007/978-3-662-43539-7_8
• 发表时间: 2014
• 作者: T. Koizumi;T. Kanbara