Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis

被引：1397

作者：

Hoyle, Charles E. ^{[3
]}

Lowe, Andrew B. ^{[2
]}

Bowman, Christopher N. ^{[1
]}

机构：

[1] Univ Colorado, Dept Chem & Biol Engn, Boulder, CO 80309 USA

[2] Univ New S Wales, Sch Chem Sci & Engn, CAMD, Sydney, NSW 2052, Australia

[3] Univ So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USA

来源：

CHEMICAL SOCIETY REVIEWS | 2010年 / 39卷 / 04期

关键词：

CONJUGATE ADDITION; YNE REACTIONS; ENE; PHOTOPOLYMERIZATIONS; POLY(N; N-DIETHYLACRYLAMIDE); EFFICIENT; KINETICS; FACILE; ROUTE; FILMS;

D O I：

10.1039/b901979k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The merits of thiol-click chemistry and its potential for making new forays into chemical synthesis and materials applications are described. Since thiols react to high yields under benign conditions with a vast range of chemical species, their utility extends to a large number of applications in the chemical, biological, physical, materials and engineering fields. This critical review provides insight into emerging venues for application as well as new mechanistic understanding of this exceptional chemistry in its many forms (81 references).

引用

页码：1355 / 1387

页数：33

共 81 条

[1] Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis [J].

Abe, Aki M. M. ;

Sauerland, Sami J. K. ;

Koskinen, Ari M. P. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5411-5413

[2] Click Chemistry beyond Metal-Catalyzed Cycloaddition [J].

Becer, C. Remzi ;

Hoogenboom, Richard ;

Schubert, Ulrich S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (27) :4900-4908

[3] Clicking Pentafluorostyrene Copolymers: Synthesis, Nanoprecipitation, and Glycosylation [J].

Becer, C. Remzi ;

Babiuch, Krzysztof ;

Pilz, David ;

Hornig, Stephanie ;

Heinze, Thomas ;

Gottschaldt, Michael ;

Schubert, Ulrich S. .

MACROMOLECULES, 2009, 42 (07) :2387-2394

[4] Development of thermal and photochemical strategies for thiol-ene click polymer functionalization [J].

Campos, Luis M. ;

Killops, Kato L. ;

Sakai, Ryosuke ;

Paulusse, Jos M. J. ;

Damiron, Denis ;

Drockenmuller, Eric ;

Messmore, Benjamin W. ;

Hawker, Craig J. .

MACROMOLECULES, 2008, 41 (19) :7063-7070

[5] Thiol-norbornene materials:: Approaches to develop high Tg thiol-ene polymers [J].

Carioscia, Jacquelyn A. ;

Schneidewind, Lauren ;

O'Brien, Casey ;

Ely, Robert ;

Feeser, Caitlin ;

Cramer, Neil ;

Bowman, Christopher N. .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (23) :5686-5696

[6] Evaluation and control of thiol-ene/thiol-epoxy hybrid networks [J].

Carioscia, Jacquelyn A. ;

Stansbury, Jeffrey W. ;

Bowman, Christopher N. .

POLYMER, 2007, 48 (06) :1526-1532

[7]

Chan J., in preparation

[8] Convergent synthesis of 3-arm star polymers from RAFT-prepared poly(N,N-diethylacrylamide) via a thiol-ene click reaction [J].

Chan, Justin W. ;

Yu, Bing ;

Hoyle, Charles E. ;

Lowe, Andrew B. .

CHEMICAL COMMUNICATIONS, 2008, (40) :4959-4961

[9] The nucleophilic, phosphine-catalyzed thiol-ene click reaction and convergent star synthesis with RAFT-prepared homopolymers [J].

Chan, Justin W. ;

Yu, Bing ;

Hoyle, Charles E. ;

Lowe, Andrew B. .

POLYMER, 2009, 50 (14) :3158-3168

[10] Photopolymerization of Thiol-Alkynes: Polysulfide Networks [J].

Chan, Justin W. ;

Zhou, Hui ;

Hoyle, Charles E. ;

Lowe, Andrew B. .

CHEMISTRY OF MATERIALS, 2009, 21 (08) :1579-1585

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