文献类型：期刊文献

英文题名：A simple method for N-arylation of secondary amides/amines through a NaH-initiated aryne generation strategy

作者：Jiang, Yuanrui[1,2];Zhu, Wenjing[1,2];Huang, Jiawen[1,2];Luo, Fan[3];Chen, Xiaobei[4,5];Fang, Chunhui[1,2];Chen, Xin[1,2];Liu, Shihui[3];Hu, Yanwei[1,2];Zhang, Shilei[1,2]

机构：[1]Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[2]Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[3]Jiaxing Univ, Coll Med, 118 Jiahang Rd, Jiaxing 314001, Peoples R China;[4]East China Univ Sci Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Me, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[5]East China Univ Sci Technol, Sch Pharm, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China

年份：2023

卷号：11

期号：1

起止页码：12

外文期刊名：ORGANIC CHEMISTRY FRONTIERS

收录：;EI(收录号：20234314928192);WOS:【SCI-EXPANDED(收录号:WOS:001082297200001)，CCR-EXPANDED(收录号:WOS:001082297200001)】；

基金：This work was supported by the National Natural Science Foundation of China (22271206 and 22071053), East China University of Science and Technology, the '111' Project and PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions).

语种：英文

外文关键词：Amides - Aromatic compounds - Chemical reactions - Hydrides - Sodium compounds - Transition metals

摘要：A very simple and practical method has been uncovered for N-arylation of many sets of secondary amides/amines. The reaction could be easily conducted in a vial without the use of strictly anhydrous reagents and/or an inert atmosphere. This transition metal-free coupling reaction was based on the use of our previously reported novel aryne generation system: a combination of o-diiodoarene and sodium hydride. In our protocol, sodium hydride acts as an iodophile by forming a neighboring-group-assisted transition state with o-diiodoarene, which greatly enhances the metal-halogen exchange process. o-Diiodoarene has two roles in the reaction: (i) as an aryne precursor to produce an aryne at near room temperature and (ii) as an electrophilic iodine donor to support the generation of the final o-iodoaryl product. The generality of the method is demonstrated by 99 examples containing almost all kinds of amides and amines.