Aerobic, Diselenide-Catalyzed Redox Dehydration: Amides and Peptides

被引：31

作者：

Akondi, Srirama Murthy ^{[1
]}

Gangireddy, Pavankumar ^{[1
,2
]}

Pickel, Thomas C. ^{[1
]}

Liebeskind, Lanny S. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA

[2] NIPER Hyderabad, Med Chem Dept, Hyderabad 500037, Telangana, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 03期

基金：

美国国家科学基金会;

关键词：

OXIDATION-REDUCTION-CONDENSATION; CARBOXYLIC-ACIDS; MITSUNOBU REACTIONS; BOND FORMATION; ORGANOSELENIUM COMPOUNDS; BORROWING HYDROGEN; SELENIUM; AMINES; ACTIVATION; CHEMISTRY;

D O I：

10.1021/acs.orglett.7b03620

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

At 2.5 mol % loadings using reaction temperatures between 30-55 degrees C, ortho-functionalized diaryl diselenides are highly effective organocatalytic oxidants for aerobic redox dehydrative amidic and peptidic bond formation using triethyl phosphite as a simple terminal reductant. This simple-to-perform organocatalytic reaction relies on the ability of selenols to react directly with dioxygen in air without recourse to metal catalysts. It represents an important step toward the development of a general, economical, and benign catalytic redox dehydration protocol.

引用

页码：538 / 541

页数：4

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