Phosphorus fluoride exchange: Multidimensional catalytic click chemistry from phosphorus connective hubs

Sun, S, Homer, JA, Smedley, CJ, Cheng, QQ, Sharpless, KB, Moses, JE (August 2023) Phosphorus fluoride exchange: Multidimensional catalytic click chemistry from phosphorus connective hubs. Chem, 9 (8). pp. 2128-2143. ISSN 2451-9308

DOI: 10.1016/j.chempr.2023.05.013

Abstract

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.

Item Type: Paper
Subjects: chemistry
chemistry > techniques > click chemistry
chemistry > techniques
CSHL Authors:
Communities: CSHL labs > Moses lab
CSHL Cancer Center Program
CSHL Cancer Center Program > Cellular Communication in Cancer Program
SWORD Depositor: CSHL Elements
Depositing User: CSHL Elements
Date: 10 August 2023
Date Deposited: 28 Sep 2023 17:29
Last Modified: 30 Apr 2024 18:10
Related URLs:
URI: https://repository.cshl.edu/id/eprint/41030

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