Electrooxidative Synthesis of Bis- and Oligoarenes

双芳烃和低聚芳烃的电氧化合成

• 批准号: 286171883
• 负责人: Professor Dr. Siegfried R. Waldvogel
• 金额: --
• 依托单位: Institut für Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2015
• 资助国家: 德国
• 起止时间: 2014-12-31 至 2018-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/286171883?language=en
• 关键词: Electrooxidative; Synthesis; Bis; Oligoarenes

In this joint project, the mechanism and scope of a new electrooxidative biaryl coupling of substituted arenes will be explored and defined. This electrochemical approach has the advantage that no leaving functionalities are required for biaryl cross-coupling. Since no reagent waste is formed in this reagent- and metal-free electroorganic process, a highly sustainable synthetic method will be established. The use of electricity and solvent effects to direct the selectivity of the cross-coupling creates a cutting-edge technique in contemporary organic synthesis. This innovative cross-coupling concept based on the decoupling of nucleophilicity and oxidation potential the substrates can be considered as a new type of umpolung and is the source of the outstanding coupling selectivity. The efficiency of this new methodology will be exploited for the efficient and modular synthesis of mimetics for a-helices based on teraryl and quateraryl architectures. The strategy involves a complementary combination of modern metal-catalyzed steps as well as electrosynthetic transformations which do not require leaving functionalities and provide a direct and sustainable access to such entities.

在这个合作项目中，一种新的取代芳烃的电氧化联芳基偶联的机制和范围将被探索和定义。这种电化学方法的优点是联芳基交叉偶联不需要离去官能团。由于在这种无试剂和无金属的电有机过程中不会形成试剂废物，因此将建立高度可持续的合成方法。利用电和溶剂效应来指导交叉偶联的选择性，在当代有机合成中创造了一种尖端技术。这种基于亲核性和氧化电位的解耦的创新交叉偶联概念可以被认为是一种新型的upolung，并且是杰出的偶联选择性的来源。这种新方法的效率将被利用的有效和模块化的合成的模拟物的α-螺旋的基础上teraryl和quateraryl架构。该战略涉及现代金属催化步骤以及电合成转化的互补组合，这些步骤不需要离开官能团，并提供直接和可持续的途径。

项目成果

Electrochemical Synthesis of 2-Hydroxy-para-terphenyls by Dehydrogenative Anodic C–C Cross-Coupling Reaction

• DOI: 10.1055/s-0037-1611942
• 发表时间: 2019-01
• 期刊: Synlett
• 影响因子: 2
• 作者: S. Lips;R. Franke;S. Waldvogel

The Catalytic Effect of Fluoroalcohol Mixtures Depends on Domain Formation

• DOI: 10.1021/acscatal.6b03090
• 发表时间: 2017-03-01
• 期刊: ACS CATALYSIS
• 影响因子: 12.9
• 作者: Holloczki, Oldamur;Berkessel, Albrecht;Kirchner, Barbara
• 通讯作者: Kirchner, Barbara

Electro-organic Synthesis as a Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols

• DOI: 10.1055/s-0036-1588610
• 发表时间: 2017-01-01
• 期刊: SYNTHESIS-STUTTGART
• 影响因子: 2.6
• 作者: Riehl, Barbara;Dyballa, Katrin M.;Waldvogel, Siegfried R.
• 通讯作者: Waldvogel, Siegfried R.

Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.

• DOI: 10.1002/anie.201708946
• 发表时间: 2017-11
• 期刊: Angewandte Chemie
• 作者: A. Wiebe;S. Lips;D. Schollmeyer;R. Franke;S. Waldvogel