Sequential phosphine-catalyzed, nucleophilic thiol ene/radical-mediated thiol-yne reactions and the facile orthogonal synthesis of polyfunctional materials

The first example of highly efficient sequential thiol-ene/thiol-yne reactions conducted in an orthogonal manner is presented and its broad application in the synthesis of polyfunctional materials demonstrated. The anionic chain mechanism of the phosphine-mediated thiol-ene reaction is highlighted,...

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Bibliographic Details
Main Authors: Chan, J., Hoyle, C., Lowe, Andrew
Format: Journal Article
Published: American Chemical Society 2009
Online Access:http://hdl.handle.net/20.500.11937/35667
Description
Summary:The first example of highly efficient sequential thiol-ene/thiol-yne reactions conducted in an orthogonal manner is presented and its broad application in the synthesis of polyfunctional materials demonstrated. The anionic chain mechanism of the phosphine-mediated thiol-ene reaction is highlighted, as is the radical-mediated thiol-yne reaction. Kinetic data for a model reaction are presented, followed by a discussion of the synthesis of a range of materials with diverse functionality, including an example of potential biomedical significance. © 2009 American Chemical Society.