文献类型：期刊文献

英文题名：Orthogonal sp3 C1-H and N-H Bond Functionalization of 1,2,3,4-Tetrahydroisoquinolines via the Ugi Four-Component Reaction

作者：Yan, Ji-Min[1]; Bai, Qi-Fan[1]; Xu, Chang[1]; Feng, Gaofeng[1]

机构：[1] Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, 312000, China

年份：2016

卷号：48

期号：21

起止页码：3730

外文期刊名：Synthesis (Germany)

收录：EI(收录号：20163002633407)、Scopus(收录号：2-s2.0-84978780357)

语种：英文

外文关键词：1,2,3,4-tetrahydroisoquinolines; iminium isomerization; redox-neutral reaction; sp³ C-H functionalization; Ugi reaction

外文摘要：A new protocol for orthogonal sp3 C1-H and N-H bond functionalization of 1,2,3,4-tetrahydroisoquinolines has been established via the Ugi four-component reaction with aldehydes, isonitriles, and carboxylic acids. It was revealed that only the N-H bond could be functionalized when the reaction was performed in acetonitrile at room temperature; however, when the reaction was carried out in toluene at 80 °C, redox-neutral sp3 C1-H bond functionalization of 1,2,3,4-tetrahydroisoquinolines was achieved. Differing from the common role of carboxylic acid as a promoter in redox-neutral amine α-functionalization, the carboxylic acid employed herein is also a reactant. The orthogonal process is compatible with various substrates and provides an appealing access to a library of structurally diverse 1,2,3,4-tetrahydroisoquinolines.