School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
Org Biomol Chem. 2023 May 24;21(20):4216-4219. doi: 10.1039/d3ob00438d.
A Lewis acid-catalyzed electrophilic dearomatizative thiocyanation and cyclization of benzofurans with -thiocyanatosuccinimide has been accomplished by Lewis acid catalysis with CuOTf under mild conditions. It was suggested that the electrophilic thiocyanating reagent was activated by CuOTf, and difunctionalization was achieved through a thiocyanation/spirocyclization pathway. Thus, a series of thiocyanato-containing spiroketals were obtained in moderate to high yields. It provides an alternative approach for the synthesis of functionalized [6,5]/[5,5]-spiroketals.
Lewis 酸催化的苯并呋喃与 - 异硫氰酸琥珀酰亚胺的亲电去芳构化硫氰化和环化反应已经通过 Lewis 酸催化在温和条件下用 CuOTf 完成。据推测，亲电硫氰化试剂被 CuOTf 激活，通过硫氰化/螺环化途径实现双官能化。因此，一系列含有硫氰基的螺缩酮以中等至高产率得到。它为功能化 [6,5]/[5,5]-螺缩酮的合成提供了一种替代方法。
