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Iron-catalyzed azidation of cyclobutanol by C[sbnd]C bond cleavage
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2024-03-19 , DOI: 10.1016/j.tetlet.2024.155016
Xiaoyuan Liu , Limei Wang , Jincheng Zhan , Shutao Sun , Lei Liu , Wei Li , Qian Wan

An iron-catalyzed ring-opening azidation of cyclobutanols through CC bond cleavage is disclosed for the first time. A range of tertiary cyclobutanols are tolerated providing γ-carbonyl-containing secondary alkyl azides. The method provides a straightforward approach for introducing azide group into aliphatic chain of organic molecules. A plausible mechanism involving radical-mediated sequential CC bond cleavage and C−N bond formation is proposed.

中文翻译:

铁催化 C[sbnd]C 键断裂叠氮化环丁醇

首次公开了铁催化环丁醇通过CC键断裂的开环叠氮化反应。可以耐受一系列叔环丁醇,提供含γ-羰基的仲烷基叠氮化物。该方法提供了一种将叠氮基引入有机分子的脂肪链中的简单方法。提出了一种涉及自由基介导的连续 CC 键断裂和 CN 键形成的合理机制。
更新日期:2024-03-19
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