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

被引：1
|
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
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 08期
基金：
中国国家自然科学基金;
关键词：
KETENIMINIUM SALTS; ARYLATION; HYDRATION; SULFONIUM; EFFICIENT; LIGANDS; SULFUR; ALKYL;
D O I：
10.1021/acs.orglett.2c00334
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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.
引用
收藏
页码：1700 / 1705
页数：6
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