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Vanadium Catalyst in Micelles: Toward a Greener Aerobic Oxidative Cleavage of Vicinal Diols in Water
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2023-06-01 , DOI: 10.1021/acssuschemeng.3c01820 Romain Carpentier 1 , William Denis 1, 2 , Fátima Sanz Azcona 2 , Davide Carraro 2 , Glenn Grauwels 1 , Manuel Orlandi 2 , Cristiano Zonta 2 , Giulia Licini 1, 2 , Kristin Bartik 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2023-06-01 , DOI: 10.1021/acssuschemeng.3c01820 Romain Carpentier 1 , William Denis 1, 2 , Fátima Sanz Azcona 2 , Davide Carraro 2 , Glenn Grauwels 1 , Manuel Orlandi 2 , Cristiano Zonta 2 , Giulia Licini 1, 2 , Kristin Bartik 1
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Aqueous micellar media offer an alternative to organic solvents for the development of safe and environmentally benign synthesis. A vanadium aminotriphenolate complex, known to be an effective catalyst for the aerobic oxidative C–C cleavage of vicinal diols in organic solvents, was incorporated in zwitterionic dodecyl phosphocholine (DPC) and in mixed TPGS-750-M:DPC micelles. It efficiently performed affording the corresponding carbonyl derivatives with no overoxidation, with catalyst loading down to 0.2 mol % and reaching TONs up to 500. The mixed micelles, which combine the enhanced stability conferred by zwitterionic DPC and the exceptional extraction properties of non-ionic TPGS-750-M, could be recycled and full conversion achieved upon reloading with catalyst and substrate. The study of the correlation between the reactivity of different substrates and their local concentration in the micellar core, derived from DOSY experiments, highlights that, while lipophilicity is important, the ease with which the substrate can access the catalyst, and therefore the location of the catalyst in the micellar phase, must also be considered when trying to rationalize reactivity in micelles.
中文翻译：
胶束中的钒催化剂：实现水中邻位二醇的绿色有氧氧化裂解
水性胶束介质为开发安全和环境友好的合成提供了有机溶剂的替代品。一种氨基三酚钒复合物，已知是有机溶剂中邻二醇有氧氧化 C-C 裂解的有效催化剂，被掺入两性离子十二烷基磷酸胆碱 (DPC) 和混合 TPGS-750-M:DPC 胶束中。它有效地提供了相应的羰基衍生物而没有过氧化，催化剂负载量低至 0.2 mol% 并达到高达 500 的 TON。混合胶束结合了两性离子 DPC 赋予的增强稳定性和非离子 TPGS 的卓越萃取性能-750-M，可以回收利用，并在重新加载催化剂和底物后实现完全转化。
更新日期：2023-06-01
中文翻译：
胶束中的钒催化剂：实现水中邻位二醇的绿色有氧氧化裂解
水性胶束介质为开发安全和环境友好的合成提供了有机溶剂的替代品。一种氨基三酚钒复合物，已知是有机溶剂中邻二醇有氧氧化 C-C 裂解的有效催化剂，被掺入两性离子十二烷基磷酸胆碱 (DPC) 和混合 TPGS-750-M:DPC 胶束中。它有效地提供了相应的羰基衍生物而没有过氧化，催化剂负载量低至 0.2 mol% 并达到高达 500 的 TON。混合胶束结合了两性离子 DPC 赋予的增强稳定性和非离子 TPGS 的卓越萃取性能-750-M，可以回收利用，并在重新加载催化剂和底物后实现完全转化。
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