Pd(II)-catalyzed Alkylation of Arenes and Hetarenes

Pd(II) 催化的芳烃和杂烃的烷基化

• 批准号: 242472260
• 负责人: Professor Dr. Thorsten Bach
• 金额: --
• 依托单位: Lehrstuhl für Organische Chemie I
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2013
• 资助国家: 德国
• 起止时间: 2012-12-31 至 2017-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/242472260?language=en
• 关键词: Pd; II; catalyzed; Alkylation; Arenes

The project aims at a selective alkylation of hetarenes and arenes employing an alkyl halide and a Pd(II) catalyst. The additive norbornene should - as previously shown for indoles - induce a regioselective alkylation of NH-acidic heterocycles (e.g. pyrrole, imidazole, pyrazole, benzimidazole, 4-pyridone) via a strained palladacycle. Applications in natural product total synthesis should demonstrate the utility and brevity of the new method. Upon chiral modification of norbornene, stereoselective processes (enantiotopos differentiation, kinetic resolution) will be studied for the first time in this type of C-H activation reactions. In mechanistically related reactions, it is planned by an appropriate choice of the directing group to achieve an ortho selective or - upon addition of norbornene - a meta selective alkylation of aromatic hydrocarbons.

该项目旨在采用烷基卤化物和钯（II）催化剂选择性烷基化六烯和芳烃。添加剂降冰片烯应该——正如先前对吲哚所示——通过张力环诱导nh -酸性杂环（如吡咯、咪唑、吡唑、苯并咪唑、4-吡酮）的区域选择性烷基化。在天然产物全合成中的应用应证明新方法的实用性和简洁性。对降冰片烯进行手性修饰后，首次研究了这类C-H活化反应的立体选择过程（对映异构分化、动力学分辨）。在机械相关的反应中，通过适当选择导向基团来实现邻位选择性或在加入降冰片烯后实现芳烃的间选择性烷基化。

项目成果

Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles.

• DOI: 10.1021/acs.orglett.6b00141
• 发表时间: 2016-02
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: J. Wiest;Alexander Poethig;T. Bach

Rhodium-CatalyzedN-tert-Butoxycarbonyl (Boc) Amination by Directed CH Bond Activation

• DOI: 10.1002/adsc.201600410
• 发表时间: 2016-06
• 期刊: Advanced Synthesis & Catalysis
• 影响因子: 5.4
• 作者: Julian Wippich;Nadina Truchan;T. Bach

A Route to 2-Substituted 3-Cyanopyrroles: Synthesis of Danaidal and Suffrutine A.

2-取代 3-氰基吡咯的合成路线：Danaidal 和 Suffrutine A 的合成

• DOI: 10.1021/acs.joc.6b01298
• 发表时间: 2016
• 期刊: The Journal of organic chemistry
• 作者: J. M. Wiest;T. Bach
• 通讯作者: T. Bach

C-H alkylation reactions of indoles mediated by Pd(ii) and norbornene: applications and recent developments.

• DOI: 10.1039/c8ob01025k
• 发表时间: 2018-08
• 期刊: Organic & biomolecular chemistry
• 影响因子: 3.2
• 作者: M. Wegmann;Michael Henkel;T. Bach

Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process

• DOI: 10.1055/s-0033-1338523
• 发表时间: 2013-09
• 期刊: Synthesis
• 作者: L. Jiao;T. Bach