Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest, 1420, Braine-L'Alleud, Belgium.
Angew Chem Int Ed Engl. 2017 Dec 22;56(52):16602-16605. doi: 10.1002/anie.201710445. Epub 2017 Dec 5.
Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon-carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp )-C(sp ) cross-coupling processes, with excellent functional-group tolerance.
最近，硼酸和重氮化合物的偶联反应作为一种强大的无金属碳-碳键形成方法而出现。然而，由于难以温和地形成不稳定的重氮化合物，迄今为止限制了它们的广泛应用和转化范围。在这里，我们报告了使用流动 UV 光解将噁二嗪啉作为不稳定重氮化合物家族的前体生成的应用，并首次将其用于发散的原脱硼和氧化 C(sp )-C(sp )交叉偶联反应，具有优异的官能团耐受性。
