Bissonnette Noah B, Bisballe Niels, Tran Andrew V, Rossi-Ashton James A, MacMillan David W C
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
J Am Chem Soc. 2024 Mar 27;146(12):7942-7949. doi: 10.1021/jacs.4c00557. Epub 2024 Mar 12.
Here we report the design of a general, redox-switchable organophosphorus alkyl radical trap that enables the synthesis of a broad range of C()-P(V) modalities. This "plug-and-play" approach relies upon activation of alcohols and O═P(R)H motifs, two broadly available and inexpensive sources of molecular complexity. The mild, photocatalytic deoxygenative strategy described herein allows for the direct conversion of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs. This includes the facile incorporation of medicinally relevant phosphonate ester prodrugs.
在此，我们报道了一种通用的、氧化还原可切换的有机磷烷基自由基捕获剂的设计，该捕获剂能够合成多种C()-P(V)化合物。这种“即插即用”方法依赖于醇和O═P(R)H基序的活化，这是两种广泛可得且廉价的分子复杂性来源。本文所述的温和光催化脱氧策略允许将糖类、核苷和复杂药物结构直接转化为它们的有机磷类似物。这包括轻松引入具有药用相关性的膦酸酯前药。
