Wang Zifei, Vishwakarma Dharmendra S, Sun Shoujun, Huang Qiyao, Pati Soumyaranjan, Johnson Robert M, Rufrano Michael R, Gembicky Milan, Homer Joshua A, Moses John E
Cancer Center, Cold Spring Harbor Laboratory, 1 Bungtown Road, Cold Spring Harbor, NY 11724, USA.
Department of Chemistry, Stony Brook University, Nicolls Road, Stony Brook, NY 11794, USA.
Adv Synth Catal. 2025 Apr 1;367(7). doi: 10.1002/adsc.202401573. Epub 2025 Jan 7.
Phosphorus Fluoride Exchange (PFEx) is a new click chemistry technology that hinges on the creation of innovative hubs to unlock its potential and broaden its applications. In this study, we outline some guiding principles for PFEx hub development and validate these principles by developing a new hub, 2-substituted-alkynyl-1-cyclotriphosphazenes (SACPs). These SACPs serve as versatile PFEx hubs with stable functionality and orthogonal reactivity, exemplifying their utility within the Diversity Oriented Clicking (DOC) framework. We demonstrate that SACPs interact with various 1,3-dipoles, enabling the synthesis of phosphorus-rich compounds through sequential cycloaddition and PFEx reactions, thus pioneering new synthetic routes for wide application of click chemistry.
磷氟交换(PFEx)是一种新型的点击化学技术,它依赖于创建创新的核心来释放其潜力并拓宽其应用范围。在本研究中,我们概述了PFEx核心开发的一些指导原则,并通过开发一种新的核心——2-取代-炔基-1-环三磷腈(SACPs)来验证这些原则。这些SACPs作为多功能的PFEx核心,具有稳定的官能团和正交反应性,例证了它们在多样性导向点击(DOC)框架内的实用性。我们证明SACPs与各种1,3-偶极子相互作用,通过连续的环加成和PFEx反应实现富磷化合物的合成,从而开创了点击化学广泛应用的新合成路线。