Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.
Chemistry. 2012 Jan 23;18(4):1187-93. doi: 10.1002/chem.201102680. Epub 2011 Dec 21.
An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed. The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant such as I(2) or 2-iodoxybenzoic acid (IBX)-SO(3)K/NaI. In particular, the latter method, as a new and well-balanced oxidizing agent, shows excellent functional group tolerance and substrate scope and thus allows access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds that would be more difficult to access by using traditional methods. Because the azide-containing products easily undergo 1,3-dipolar cycloaddition with alkynes, our report represents a novel route to analogues of sensitive complex molecules.
一种操作简单、直接的 1,3-二羰基化合物的叠氮化反应已经被开发出来。该反应在环境条件下，使用叠氮化钠和碘基氧化剂（如 I(2)或 2-碘代苯甲酸（IBX）-SO(3)K/NaI），就能顺利进行。特别是后一种方法，作为一种新型的、平衡良好的氧化剂，表现出极好的官能团耐受性和底物范围，因此能够获得各种叔 2-叠氮基和 2,2-双叠氮基 1,3-二羰基化合物，而使用传统方法则更难获得这些化合物。由于含叠氮化物的产物容易与炔烃发生 1,3-偶极环加成反应，因此我们的报告代表了一种获得敏感复杂分子类似物的新途径。
