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Aerobic, Diselenide-Catalyzed Redox Dehydration: Amides and Peptides
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-11 00:00:00 , DOI: 10.1021/acs.orglett.7b03620
Srirama Murthy Akondi 1 , Pavankumar Gangireddy 1 , Thomas C. Pickel 1 , Lanny S. Liebeskind 1
Affiliation  

At 2.5 mol % loadings using reaction temperatures between 30–55 °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.

中文翻译:

有氧,二硒化物催化的氧化还原脱水:酰胺和多肽

在反应温度为30-55°C的条件下,负载量为2.5 mol%时,邻官能化的二芳基二硒化物是高效的有机催化氧化剂,可利用亚磷酸三乙酯作为简单的末端还原剂来形成需氧氧化还原脱水的酰胺和肽键。这种简单易行的有机催化反应依赖于硒醇与空气中的双氧直接反应而不依赖金属催化剂的能力。它代表了开发通用,经济且良性的催化氧化还原脱水方案的重要一步。
更新日期:2018-01-11
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