Tetrafluorophenol-activated resins

The Development and Application of Tetrafluorophenol-Activated Resins for Rapid Amine Derivatization... 

Salvino JM, Kumar NV, Orton E, Airey J, Kiesow T, Crawford K., Mathew R, KroUkowski P, Drew M, Engers D, Kro-likowski D, Herpin T, Gardyan M, McGeehan G, Labaudiniere R. Polymer-supported tetrafluorophenol a new activated resin for chemical library synthesis. J. Comb. Chem. 2000 2 691-697. Baxendale IR, Ley SV. Polymer-supported reagents for multi-step organic synthesis appUcation to the synthesis of sildenafil. Bioorg. Med. Chem. Lett. 2000 10 1983-1986. 

Scheme 7.25 Preparation of tetrafluorophenol-containing resin 79 and formation of its active esters.

A basic example to illustrate the capture-release strategy is the use of a supported tetrafluorophenol moiety for the synthesis of amide libraries in solution. As shown in Scheme 6, a carboxylic acid is first activated with the corresponding resin-bound tetrafluorophenol ester (capture step), which in a second step reacts with nucleophilic amine (release step). 

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