School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.
Org Biomol Chem. 2021 Jun 28;19(24):5368-5376. doi: 10.1039/d1ob00842k. Epub 2021 May 28.
An efficient method for oxidative trifluoromethylselenolation/N-acylation of indoles with excess [MeN][SeCF] in the presence of acyl peroxides and their derivatives is described. The reaction is easy to handle, proceeds smoothly at room temperature under metal-free conditions, and shows advantages such as good functional group tolerance, excellent regioselectivity, and compatibility of a number of substrates, producing 1-acyl and 3-trifluoromethylselanyl substituted indoles in good yields. Acyl peroxides and peroxycarboxylic acid behave as both oxidants and acyl sources in the transformation. This one-pot procedure provides a convenient access to a new class of indole derivatives, representing the first trifluoromethylselanyl bifunctionalization of indoles with the nucleophilic [MeN][SeCF] reagent.
本文描述了一种在酰基过氧化物及其衍生物存在下，利用过量的[MeN][SeCF]，将吲哚高效氧化三氟甲基硒化/N-酰化的方法。该反应操作简单，在无金属条件下于室温下顺利进行，具有良好的官能团耐受性、优异的区域选择性和多种底物的兼容性等优点，以良好的收率得到 1-酰基和 3-三氟甲基硒代取代的吲哚。酰基过氧化物和过氧羧酸在转化中既充当氧化剂又充当酰基源。该一锅法为一类新的吲哚衍生物提供了便捷的合成途径，代表了亲核[MeN][SeCF]试剂对吲哚的首例三氟甲基硒基双官能化反应。
