Thiol-Ene Click Chemistry

Following Sharpless′ visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thio...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 49; no. 9; pp. 1540 - 1573
Main Authors Hoyle, Charles E, Bowman, Christopher N
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 22.02.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects
Acrylates - chemistry
Biocompatible Materials - chemistry
click chemistry
Dendrimers - chemical synthesis
Dendrimers - chemistry
Free Radicals - chemistry
Michael additions
Nanostructures - chemistry
Photochemical Processes
polymerization
Polymers - chemistry
Sulfhydryl Compounds - chemistry
Sulfhydryl Compounds - toxicity
Surface Properties
synthesis design
thiol-ene reaction
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Summary:Following Sharpless′ visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thiol-ene reaction as one such click reaction. This reaction has all the desirable features of a click reaction, being highly efficient, simple to execute with no side products and proceeding rapidly to high yield. Further, the thiol-ene reaction is most frequently photoinitiated, particularly for photopolymerizations resulting in highly uniform polymer networks, promoting unique capabilities related to spatial and temporal control of the click reaction. The reaction mechanism and its implementation in various synthetic methodologies, biofunctionalization, surface and polymer modification, and polymerization are all reviewed.
Bibliography:http://dx.doi.org/10.1002/anie.200903924
This manuscript is dedicated to Charles Hoyle, who passed away on September 7, 2009, while working on revisions to this manuscript. His work on thiol-ene chemistry and his passion and enthusiasm for that chemistry was legendary. He was a dedicated husband, father, and advisor, and a brilliant scientist who is missed by all who knew him.
National Institutes of Health
ArticleID:ANIE200903924
ark:/67375/WNG-9JT0C8W7-G
istex:97B32BB8BCA63540859DC18C43C915BC2C64673D
National Science Foundation
Deceased.
This manuscript is dedicated to Charles Hoyle, who passed away on September 7, 2009, while working on revisions to this manuscript. His work on thiol–ene chemistry and his passion and enthusiasm for that chemistry was legendary. He was a dedicated husband, father, and advisor, and a brilliant scientist who is missed by all who knew him.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200903924