文献类型：期刊文献

英文题名：Synthesis of α-Aryl Primary Amides from α-Silyl Nitriles and Aryl Sulfoxides through [3,3]-Sigmatropic Rearrangement

作者：Luo, Fan[1,2];Zhou, Hui[3,4,5];Chen, Xiao-Bei[1,2];Liu, Xue-Jun[6];Chen, Xiao-Dong[6];Qian, Peng-Fei[7];Wu, Xin-Ping[3,4,5];Wang, Wei[8,9];Zhang, Shi-Lei[10,11]

机构：[1]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Me, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Sch Pharm, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Ctr Computat Chem, Shanghai 200237, Peoples R China;[4]East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Ctr Computat Chem, Shanghai 200237, Peoples R China;[5]East China Univ Sci & Technol, Res Inst Ind Catalysis, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China;[6]Shanghai Neutan Pharmaceut Co Ltd, Shanghai 200131, Peoples R China;[7]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[8]Univ Arizona, Dept Pharmacol & Toxicol, Tucson, AZ 85721 USA;[9]Univ Arizona, BIO5 Inst, Tucson, AZ 85721 USA;[10]Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, Suzhou 215123, Jiangsu, Peoples R China;[11]Soochow Univ, Coll Pharmaceut Sci, Suzhou 215123, Jiangsu, Peoples R China

年份：2022

卷号：24

期号：8

起止页码：1700

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000766225300024)，CCR-EXPANDED(收录号:WOS:000766225300024)】；

基金：This work was supported by the National Natural Science Foundation of China (22071053 and 21202112), Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission, grant 2021 Sci & Tech 03-28), the 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

摘要：A simple and efficient protocol was developed for the preparation of challenging alpha-aryl primary amides. This metal-free coupling process was triggered by TfOH-promoted electrophilic activation of alpha-silyl nitrile to generate keteniminium ion species, followed by reaction with aryl sulfoxide through [3,3]-sigmatrophic rearrangement to provide the target product. To the best of our knowledge, alpha-silyl nitrile has been rarely used as a pro-electrophilic reagent. Computational investigations confirmed the transient existence of a highly electrophilic keteniminium intermediate.