作者:Madanodaya Sundhoro、Seaho Jeon、Jaehyeung Park、Olof Ramström、Mingdi Yan
DOI:10.1002/anie.201705346
日期:2017.9.25
Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18 m−1 s−1 was obtained between methyl 4‐azido‐2,3,5,6‐tetrafluorobenzoate and methyl 2‐(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza‐phosphonium ylide reactions. This PFAA
我们报道了全氟芳基叠氮化物 (PFAA) 和芳基膦之间的快速施陶丁格反应,该反应在环境条件下很容易发生。在 CD 3 CN/D 2 O中,4-叠氮基-2,3,5,6-四氟苯甲酸甲酯和 2-(二苯基膦酰基)苯甲酸甲酯之间的速率常数高达 18 m -1 s -1 。亚氨基正膦产物对于水解和氮杂鏻叶立德反应是稳定的。这种PFAA施陶丁格反应被证明是一种极好的生物正交反应。PFAA 衍生的甘露糖胺和半乳糖胺成功转化为细胞表面聚糖,并用膦衍生的荧光团缀合牛血清白蛋白进行有效标记。