Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis
Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis
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DOI：
10.1021/acs.orglett.5b02240
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发表时间：
2015-10-02
期刊：
影响因子：
5.2
通讯作者：
Lipshutz, Bruce H.
中科院分区：
文献类型：
--
作者：
Isley, Nicholas A.;Linstadt, Roscoe T. H.;Lipshutz, Bruce H.
鉴于亲核芳香取代反应(SNAR)对DMF、DMSO、DMAc和NMP等偶极非质子性溶剂的巨大依赖，报道了一种简单、环保的替代方法。在水中使用一种“设计为良性”的非离子表面活性剂TPGS-750-M，使氮、氧和硫亲核试剂能够参与SNAR反应。芳香族和杂芳族底物很容易参与这种胶束催化，这种胶束催化发生在或接近环境温度。
Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.