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

页码：1700 / 1705

页数：6

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