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光致能量转移实现的烯烃无金属氨基(杂)芳基化和氨磺酰化反应

Metal-Free Amino(hetero)arylation and Aminosulfonylation of Alkenes Enabled by Photoinduced Energy Transfer.

作者信息

Qi Xu-Kuan, Zheng Meng-Jie, Yang Chao, Zhao Yating, Guo Lin, Xia Wujiong

机构信息

State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China.

College of Chemical and Material Engineering, Quzhou University, Quzhou 324000, China.

出版信息

J Am Chem Soc. 2023 Aug 2;145(30):16630-16641. doi: 10.1021/jacs.3c04073. Epub 2023 Jul 24.

Abstract

β-(Hetero)arylethylamines are privileged structural motifs found in many high-value organic molecules, including pharmaceuticals and natural products. To construct these important molecular skeletons, previous methods are mainly achieved by amino(hetero)arylation reaction with the aid of transition metals and preactivated substrates. Herein, we report a metal-free and photoinduced intermolecular amino(hetero)arylation reaction for the single-step installation of both (hetero)aryl and iminyl groups across alkenes in an efficient and regioselective manner. This method shows broad scope (up to 124 examples) and excellent tolerance of various olefins─from the simplest ethylene to complex multisubstituted alkenes can all participate in the reaction. Furthermore, aminosulfonylation of alkenes can be also conducted in the presence of sodium bisulfite as the SO source.

摘要

β-(杂)芳基乙胺是许多高价值有机分子(包括药物和天然产物)中常见的优势结构基序。为构建这些重要的分子骨架,以往的方法主要是借助过渡金属和预活化底物通过氨基(杂)芳基化反应来实现。在此,我们报道了一种无金属光诱导分子间氨基(杂)芳基化反应,该反应能够以高效且区域选择性的方式在烯烃上一步同时引入(杂)芳基和亚胺基。此方法适用范围广泛(多达124个实例),对各种烯烃具有出色的耐受性,从最简单的乙烯到复杂的多取代烯烃都能参与反应。此外,在亚硫酸氢钠作为硫源的情况下,也能进行烯烃的氨磺酰化反应。

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