The Emergence of Thiol–Ene Coupling as a Click Process for Materials and Bioorganic Chemistry

Dondoni, Alessandro

doi:10.1002/anie.200802516

Cited by 601 publications

(427 citation statements)

References 42 publications

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“…After successful discovery of click chemistry concept by Sharpless and Meldal, it is easy to perform polymer modification with high yield under mild conditions, such as rapid, stereospecific, orthogonal and no by-product coherent with the green chemistry [26]. Today, a series of reactions including Huisgen type Cu(I) catalyzed cycloaddition (CuAAC) [27,28], thiol-ene [29][30][31] and Diels-Alder [32] are recognized as well-known click chemistry reactions [33]. Modification of polymers with CuAAC click reaction is very general, robust and particularly simple compared to other click chemistry reactions [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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Abstract. Graft copolymers from commercial chlorinated polypropylene (PP-Cl) possessing either poly(ethylene glycol) (PEG) or poly(ɛ-caprolactone) (PCL) grafts are synthesized by copper (I)-catalyzed azide-alkyne cycloaddition 'click' reaction (CuAAC). For this purpose, azido-functional polypropylene is prepared by nucleophilic substitution of chlorine groups of PP-Cl with azidotrimethylsilane-tetrabutylammonium fluoride. Whereas, the clickable alkyne end-functional PEG and PCL are independently synthesized by esterification reaction of poly(ethylene glycol) methyl ether with 4-pentyonic acid at room temperature and ring-opening polymerization of ε-caprolactone using stannous octoate as catalyst and propargyl alcohol as initiator. Finally, the corresponding graft copolymers, PP-g-PEG and PP-g-PCL, with different surface properties were successfully synthesized by CuAAC 'click' reaction under mild condition. Spectral, chromatographic and thermal analyses at various stages prove the formation of desired polypropylene-based graft copolymers with well-defined properties. Furthermore, the water contact angle values of PP-Cl, PP-g-PEG and PP-g-PCL are found as 90±1°, 78±1.8° and 83±2.1°, respectively.

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Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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“…Today, thiol-ene additions (or thiol-ene click reactions) are considered as a versatile and broadly applicable tool in polymer science. [18] Nevertheless, already early on it was discovered that dithiols and dienes are suitable monomers for polymer synthesis. [19] More recent investigations have shown that quite high molecular weight polythioethers can be obtained in that way, [20] that initiators are not necessary for the reaction to proceed, [21] but radical inhibitors suppress the polymerization for some time.…”

Section: Introductionmentioning

confidence: 99%

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Türünç

Meier

2010

Macromol. Rapid Commun.

174

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Thiol‐ene additions of methyl 10‐undecenoate, a castor oil derived renewable platform chemical, were studied with the goal of preparing a set of renewable monomers. Good to excellent yields were obtained for these solvent and initiator free thiol‐ene additions. The resulting monomers were then polymerized using TBD as a catalyst, to linear as well as hyperbranched polyesters that also contain thio‐ether linkages. All thus prepared polymers were fully characterized (NMR, GPC, DSC, and TGA) and the results of these investigations will be discussed within this contribution. The thermal analysis of these polymers revealed melting points in the range from 50 to 71 °C. Moreover, no significant weight loss was observed below 300 °C.magnified image

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“…The thiol-ene click reaction has proven to be a versatile tool in organic synthesis. [12][13][14][15] In particular, such a strong nucleophilic character has been used in the thiol-Michael reaction which is exploited extensively in synthesis and polymer modification since it leads to thioesters in very high yields. 16,17 Hence, in order to verify the nucleophilicity of compound 4, it was reacted in the presence of two acrylates as shown in scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactivity of 6-mercapto-6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide

Rakotomalala¹,

Ciesielski²,

Walter³

et al. 2012

Arkivoc

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The synthesis route of the novel 6-mercapto-6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide 4 from 6-chloro-6H-dibenzo[c,e][1,2]oxaphosphinine 1 and its spectroscopic investigation are presented. In addition, reaction of the thiol group with unsaturated functionalities such as acrylates demonstrated that the newly synthesized compound could undergo thiol-ene chemistry. Moreover, modification of the reaction condition led to the formation of the rearrangement product of a thiol-Michael reaction of compound 4 with benzoquinone.

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The Emergence of Thiol–Ene Coupling as a Click Process for Materials and Bioorganic Chemistry

Abstract: The century‐old thiol–ene radical reaction is now being recognized among the ranks of other click‐type reactions (see scheme). Recent applications in dendrimer and glycopeptide syntheses demonstrate the efficiency of this process for the assembly of complex molecular systems.

Cited by 601 publications

References 42 publications

Polypropylene-based graft copolymers via CuAAC click chemistry

Polypropylene-based graft copolymers via CuAAC click chemistry

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Synthesis and reactivity of 6-mercapto-6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide

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