Switching Mechanistic Pathways by Micellar Catalysis: A Highly Selective Rhodium Catalyst for the Hydroaminomethylation of Olefins with Anilines in Water,ACS Catalysis

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Switching Mechanistic Pathways by Micellar Catalysis: A Highly Selective Rhodium Catalyst for the Hydroaminomethylation of Olefins with Anilines in Water
ACS Catalysis ( IF 11.3 ) Pub Date : 2023-02-07 , DOI: 10.1021/acscatal.2c06104
Francesca Migliorini ₁ , Elisabetta Monciatti ₁ , Giulia Romagnoli ₁ , Maria Laura Parisi ₁ , Julia Taubert ₂ , Matthias Vogt ₂ , Robert Langer ₂ , Elena Petricci ₁

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Hydroaminomethylation (HAM) is one of the most promising atom-economic processes for the production of secondary amines, which so far remains extremely challenging with anilines as substrates. Herein, we report the use of combined micellar and microwave catalysis for the HAM of olefins with anilines in water as the reaction medium that allows for the synthesis of secondary anilines in good yields and with high regioselectivities. For the micellar rhodium/xantphos catalyst system, mechanistic investigations suggest a pathway different to the commonly observed mechanisms with homogeneous catalysts for the reported HAM reaction, involving a carbonylation initiated by a C–H activation rather than classical hydroformylation steps.

中文翻译：

通过胶束催化切换机制途径：一种高选择性铑催化剂，用于烯烃与苯胺在水中的氢氨甲基化反应

氢氨甲基化 (HAM) 是生产仲胺最有前途的原子经济工艺之一，迄今为止，以苯胺为底物，这仍然极具挑战性。在此，我们报告了使用结合胶束和微波催化的烯烃 HAM 与水中的苯胺作为反应介质，可以以良好的产率和高区域选择性合成仲苯胺。对于胶束铑/黄磷催化剂系统，机理研究表明，对于报道的 HAM 反应，采用均相催化剂的常见机制不同，涉及由 C-H 活化引发的羰基化，而不是经典的加氢甲酰化步骤。

更新日期：2023-02-07

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