Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Pierre Palamini, Alexandre A. Schoepfer, Prof. Dr. Jerome Waser
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引用次数: 0

Abstract

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, enol ethers, vinyl sulfides, and dehydroamino esters, were regioselectively functionalized with an azide and nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric acids, oximes, and phenols. The method led to a more efficient synthesis of 1,2-azidofunctionalized pharmaceutical intermediates when compared to previous approaches, resulting in both reduction of step count and increase in overall yield. The scope and limitations of these transformations were further investigated through a standard unbiased selection of 15 substrate combinations out of 1,175,658 possible using a clustering technique.

Abstract Image

烯基极性交叉光催化叠氮官能化研究
基于自由基-极性交叉策略,在温和条件下使用市售原料和容易获得的试剂进行了烯烃叠氮官能化反应。广泛的烯烃,包括乙烯基芳烃、烯醚、乙烯基硫化物和脱氢氨基酯,可与叠氮化物和亲核试剂(如唑、羧酸、醇、磷酸、肟和酚)进行区域选择性功能化。与以前的方法相比,该方法可以更有效地合成1,2 -叠氮化的药物中间体,从而减少了步数并提高了总收率。通过使用聚类技术从1,175,658种可能的基质组合中选择15种标准无偏选择,进一步研究了这些转换的范围和局限性。
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来源期刊
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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