Department of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Institut für Anorganische und Analytische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstraße 30, 48149, Münster, Germany.
Org Lett. 2022 Jun 3;24(21):3823-3827. doi: 10.1021/acs.orglett.2c01382. Epub 2022 May 23.
The diastereoselective synthesis of sulfonylated indolines is reported. A palladium-catalyzed dearomative sulfination of (aza)indole-tethered aryl iodides generates reactive benzylic sulfinates. These intermediates react with electrophiles in a one-pot, two-step process to generate sulfonylated products in good yields and excellent diastereoselectivity. This three-component sequence demonstrates good scalability and can be applied toward the synthesis of sulfonamides. Additionally, further derivatizations of aryl iodide containing products furnish spiro- and alkynylated indoline products.
报道了磺酰化吲哚啉的非对映选择性合成。钯催化的（氮杂）吲哚键合芳基碘化物的去芳构化磺化生成反应性苄基磺酸盐。这些中间体在一锅两步反应中与亲电试剂反应，以高产率和优异的非对映选择性生成磺酰化产物。该三组分序列具有良好的可扩展性，可用于磺酰胺的合成。此外，含芳基碘化物的产物的进一步衍生化可得到螺环和炔基化吲哚啉产物。
