文献类型：期刊文献

英文题名：Intermolecular 1,2-Difunctionalization of Nitriles via Redox Gold Catalysis: Synthesis of Benzoxazoles and Benzimidazoles

作者：Xu, Chengzhi[1];Xu, Zhenyan[2];Chen, Yifeng[2];Chen, Ming[1];Liu, Yuanhong[3]

机构：[1]Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat & Joint Int Res & Lab Precis Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

年份：2025

卷号：31

期号：12

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20250417742836);WOS:【SCI-EXPANDED(收录号:WOS:001402380800001)，CCR-EXPANDED(收录号:WOS:001402380800001)】；

基金：We thank the National Natural Science Foundation of China (22471284), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0610000), the National Key Research and Development Program of China (2022YFC2303100). M. Chen. thanks Changzhou University for a startup fund and the financial support by NSFC/China (22101034).

语种：英文

外文关键词：gold redox catalysis; difunctionalization; nitriles; oxidative addition; heterocycles

摘要：The unprecedent gold-catalyzed intermolecular 1,2-difunctionalization of nitriles with o-iodophenols or o-iodoanilines via Au(I)/Au(III) redox catalysis has been developed, providing an expedient route to the synthesis of benzoxazoles or benzimidazoles with broad substrate scope and high functional compatibility. Mechanistic investigation reveals that the Au(III)-Ar species generated via oxidative addition of o-iodophenol to MeDalphosAu+, serves as a key intermediate. Particularly, this annulation is initiated by oxidative addition, rather than the nucleophilic attack of the phenol moiety in o-iodophenol towards the nitrile. The method was also applied to the synthesis of poly aza-heterocycles via a cascade Au(I)/Au(III) and Au(I) catalysis relay.