三组分傅克转化反应：烷基和烯基三氟甲基硫醚及烯基碘化物的合成
Three-Component Friedel-Crafts Transformations: Synthesis of Alkyl and Alkenyl Trifluoromethyl Sulfides and Alkenyl Iodides.
作者信息
Chu Duc, Ellman Jonathan A
机构信息
Department of Chemistry, Yale University, New Haven, Connecticut 04720, United States.
出版信息
Org Lett. 2022 Apr 22;24(15):2921-2925. doi: 10.1021/acs.orglett.2c00924. Epub 2022 Apr 8.
Abstract
Straightforward and mild hexafluoroisopropanol (HFIP)-mediated, metal-free, three-component Friedel-Crafts approaches are reported for the synthesis of alkenyl and alkyl trifluoromethyl sulfides from arenes, (PhSO)NSCF, and alkynes or alkenes, respectively. The transformations proceed with high regio- and stereochemical control via the initial formation of cationic thiirenium and thiiranium intermediates, respectively, followed by Friedel-Crafts reactions with the arene. A mechanistically related three-component synthesis of alkenyl iodides from arenes, alkenes, and -iodosuccinimide is also reported.
摘要
据报道，有直接且温和的六氟异丙醇（HFIP）介导的无金属三组分傅克方法，分别用于从芳烃、(PhSO)NSCF以及炔烃或烯烃合成烯基和烷基三氟甲基硫醚。这些转化过程通过分别首先形成阳离子硫杂环丙烯鎓和硫杂环丙烷鎓中间体，然后与芳烃进行傅克反应，从而实现了高度的区域和立体化学控制。还报道了一种与机理相关的由芳烃、烯烃和N-碘代琥珀酰亚胺进行的三组分合成烯基碘化物的方法。
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