Nanoparticles as Heterogeneous Catalysts for ppm Pd-Catalyzed Aminations in Water
Nanoparticles as Heterogeneous Catalysts for ppm Pd-Catalyzed Aminations in Water
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DOI：
10.1021/acssuschemeng.3c06527
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发表时间：
2024-01-22
影响因子：
8.4
通讯作者：
Lipshutz，Bruce H.
中科院分区：
文献类型：
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作者：
Iyer，Karthik;Kavthe，Rahul;Lipshutz，Bruce H.
已经开发了采用多相催化的一般方案，其能够在水胶束催化下实现ppm的Pd催化的C-N交叉偶联反应。一种新的纳米粒子催化剂含有专门连接的钯，与纳米反应器组成的设计师表面活性剂萨维，一种可生物降解的两亲物，催化C-N键形成可循环水。从高度功能化的药物相关API到Merck Informer Library的离析物，各种偶联伙伴都可以在这些对环境负责的可持续反应条件下轻松参与。与本报告相关的其他关键特征包括在产品中发现的低水平残留Pd、水性反应介质的可回收性、使用海水作为反应介质的替代来源、使用拟卤化物作为替代反应伙伴的选择以及相关的低E因子。此外，一个前所未有的5步，一锅序列，具有在制药行业中最广泛使用的几个转换，建议潜在的工业应用。
A general protocol employing heterogeneous catalysis has been developed that enables ppm of Pd-catalyzed C–N cross-coupling reactions under aqueous micellar catalysis. A new nanoparticle catalyst containing specifically ligated Pd, in combination with nanoreactors composed of the designer surfactant Savie, a biodegradable amphiphile, catalyzes C–N bond formations in recyclable water. A variety of coupling partners, ranging from highly functionalized pharmaceutically relevant APIs to educts from the Merck Informer Library, readily participate under these environmentally responsible, sustainable reaction conditions. Other key features associated with this report include the low levels of residual Pd found in the products, the recyclability of the aqueous reaction medium, the use of ocean water as an alternative source of reaction medium, options for the use of pseudohalides as alternative reaction partners, and associated lowEfactors. In addition, an unprecedented 5-step, one-pot sequence is presented, featuring several of the most widely used transformations in the pharmaceutical industry, suggesting potential industrial applications.