Development of micelle-like catalyst for aqueous-media organic synthesis

水介质有机合成胶束状催化剂的开发

• 批准号: 17550147
• 负责人: FUJITA Ken-ichi
• 金额: $ 2.3万
• 依托单位: The National Institute of Advanced Industrial Science and Technology (AIST)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2005
• 资助国家: 日本
• 起止时间: 2005 至 2006
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-17550147/
• 关键词: Diels-Alder reaction; Mannich reaction; Dendrimer; Lewis acid; ルイス酸触媒

A series of dendritic ligands with a 2,2'-bipyridine core was synthesized through the coupling of 4,4'-dihydroxy-2,2'-bipyridine with poly(arylether) dendrons. The corresponding dendritic Cu(OTf)_2 catalysts were used for Diels-Alder and three-component condensation reactions. The dendritic Cu(OTf)_2-catalyzed Diels-Alder reaction proceeded smoothly, and these dendritic catalysts could be recycled without deactivation by reprecipitation. Three-component condensation reactions such as Mannich-type reactions also proceeded not only in dichloromethane but also in water. Furthermore, a positive dendritic effect on chemical yields was observed in both Diels-Alder reactions and aqueous-media three-component condensation reactions. It was found that the immobilization of Lewis acids on dendrimers at the core position is suitable for the design of water-compatible Lewis acid catalysts.

通过4，4 ′-二羟基-2，2 ′-联吡啶与聚芳醚树枝状基元的偶联反应，合成了一系列以2，2 ′-联吡啶为核的树枝状配体。相应的树枝状Cu（OTf）_2催化剂用于Diels-Alder反应和三组分缩合反应。树枝状Cu（OTf）_2催化的Diels-Alder反应可以顺利进行，且催化剂可以重复使用而不会因再沉淀而失活。三组分缩合反应，如曼尼希型反应不仅在二氯甲烷中，而且在水中也进行。此外，在Diels-Alder反应和水介质三组分缩合反应中都观察到了对化学产率的正树枝化效应。结果表明，将刘易斯酸固定在树枝状大分子的核位上，可用于水相容性刘易斯酸催化剂的设计。

项目成果

Diels-Alder reaction using a dendritic copper(II) triflate-catalyst : a positive dendritic effect on the chemical yield

使用树枝状三氟甲磺酸铜 (II) 催化剂的狄尔斯-阿尔德反应：对化学产率的积极树枝状效应

• 发表时间: 2006
• 期刊: TETRAHEDRON LETTERS 47
• 作者: K.Oyaizu;M.Yuasa;藤田 賢一;村木 孝仁;Ken-ichi Fujita
• 通讯作者: Ken-ichi Fujita

Mannich-Type Reaction in Water, Conducted by Employing a Dendritic Copper(II) Triflate-Catalyst : a Positive Dendritic Effect on Chemical Yield

使用树枝状三氟甲磺酸铜 (II) 催化剂在水中进行曼尼希型反应：对化学产率的积极树枝状效应

• 发表时间: 2006
• 期刊: SYNLETT 16号
• 作者: K.Oyaizu;M.Yuasa;藤田 賢一;村木 孝仁
• 通讯作者: 村木 孝仁

Mannich-Type Reaction in Water, Conducted by Employing a Dendritic Copper(II) Triflate-Catalyst a Positive Dendritic Effect on Chemical Yield

使用树枝状三氟甲磺酸铜 (II) 催化剂在水中进行曼尼希型反应，对化学产率产生积极的树枝状影响

• 发表时间: 2006
• 期刊: SYNLETT 16
• 作者: K.Oyaizu;M.Yuasa;藤田 賢一;村木 孝仁;Ken-ichi Fujita;Takahito Muraki
• 通讯作者: Takahito Muraki

Diels-Alder reaction using a dendritic copper(II) triflate- catalyst : a positive dendritic effect on the chemical yield

使用树枝状三氟甲磺酸铜(II)催化剂的狄尔斯-阿尔德反应：对化学产率的积极树枝状效应

• 发表时间: 2006
• 期刊: TETRAHEDRON LETTERS 47巻28号
• 作者: K.Oyaizu;M.Yuasa;藤田 賢一
• 通讯作者: 藤田 賢一

Synthesis of novel dendritic 2,2'-bipyridine ligands and their application to Lewis acid-catalyzed diels-alder and three-component condensation reactions.

• DOI: 10.1021/jo070767a
• 发表时间: 2007-09
• 期刊: The Journal of organic chemistry
• 作者: T. Muraki;Ken-Ichi Fujita;Masato Kujime