磷
烷基
氟化物
化学
芳基
胺气处理
点击化学
组合化学
催化作用
基础(拓扑)
无机化学
有机化学
数学
数学分析
作者
Shoujun Sun,Joshua A. Homer,Christopher J. Smedley,Qian Cheng,K. Barry Sharpless,John E. Moses
出处
期刊:Chem
[Elsevier]
日期:2023-08-01
卷期号:9 (8): 2128-2143
被引量:8
标识
DOI:10.1016/j.chempr.2023.05.013
摘要
Summary
Phosphorus fluoride exchange (PFEx) represents a cutting-edge advancement in catalytic click-reaction technology. Drawing inspiration from nature's phosphate connectors, PFEx facilitates the reliable coupling of P(V)–F loaded hubs with aryl alcohols, alkyl alcohols, and amines to produce stable, multidimensional P(V)–O and P(V)–N linked products. The rate of P–F exchange is significantly enhanced by Lewis amine base catalysis, such as 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). PFEx substrates containing multiple P–F bonds are capable of selective, serial exchange reactions via judicious catalyst selection. In fewer than four synthetic steps, controlled projections can be deliberately incorporated along three of the four tetrahedral axes departing from the P(V) central hub, thus taking full advantage of the potential for generating three-dimensional diversity. Furthermore, late-stage functionalization of drugs and drug fragments can be achieved with the polyvalent PFEx hub, hexafluorocyclotriphosphazene (HFP), as has been demonstrated in prior research.
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