State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Org Lett. 2023 May 5;25(17):2964-2969. doi: 10.1021/acs.orglett.3c00641. Epub 2023 Apr 20.
Direct dehydroxytrifluoromethylthiolation of alcohols is an attractive strategy for accessing CFS-containing compounds. Herein, we report a method for dehydroxytrifluoromethylthiolation of alcohols by using the combination of hypervalent iodine(III) reagent TFTI and N-heterocyclic carbenes. This method shows excellent stereospecificity and chemoselectivity to give a product with clean inversion of the configuration of hydroxyl groups as well as can be used for late-stage modification of structurally complex alcohols. The reaction mechanism is proposed with experimental and computational evidence.
直接的醇去羟基三氟甲基化是一种很有吸引力的方法，可以用来制备含有 CFS 化合物。在此，我们报道了一种通过高价碘(III)试剂 TFTI 和 N-杂环卡宾的组合来实现醇的去羟基三氟甲基化的方法。该方法表现出极好的立体专一性和化学选择性，可以得到一个羟基构型完全反转的产物，并且可以用于结构复杂的醇的后期修饰。反应机理通过实验和计算证据得到了提出。
