Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
作者:David C. Miller、Jacob M. Ganley、Andrew J. Musacchio、Trevor C. Sherwood、William R. Ewing、Robert R. Knowles
DOI:10.1021/jacs.9b08746
日期:2019.10.23
hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature undervisiblelight irradiation in the presence of an iridium-based photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for
Pd/Et3B and Pd/Et2Zn systems promote the nucleophilic allylations of 2-aminotetrahydrofuran and 2-aminotetrahydropyran with allylic alcohols to provide omega-hydroxyhomoallylamines in high yields. The transformation is applicable to the allylation of non-protective carbohydrates, such as ribose and deoxyribose. (C) 2010 Elsevier Ltd. All rights reserved.