2008
DOI: 10.1021/om8003527
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Thiol−Ene Reaction for the Synthesis of Multifunctional Branched Organosilanes

Abstract: Various commercially available thiols react photochemically with tetravinylsilane to give the corresponding tetrasubstituted thioether compounds. The reactions are conducted in air using typical borosilicate glassware. Yields range from 64 to 100%, and purification steps, if necessary, involve simple precipitation or extraction steps. Thiol addition occurs predominantly to give the anti-Markovnikov product; amounts of Markovnikov addition range from 1 to 5%.

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Cited by 88 publications
(69 citation statements)
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“…In both cases, the synthesis was performed from compounds containing one -NH 2 group and several -NMe 2 functions, employing the typical addition of a -NH 2 moiety to the isothiocyanate function of modified FITC (5 0 -isothiocyanatefluorescein) and the quaternization with MeI of dimethylamino (-NMe 2 ) peripheral groups. The amine groups on the periphery of carbosilane dendrimers and dendrons were introduced by thiol-ene click chemistry, which is a simple procedure to achieve this goal in carbosilane dendritic molecules with high yields [57][58][59][60]. The reaction of vinyl dendrimers GnO 3 V m (n = 1, m = 6; n = 2, m = 12; n = 3, m = 24) [59] with one equivalent of cysteamine hydrochloride HS(CH 2 ) 2 NH 3 Cl, under UV irradiation, enabled the introduction of one of these functions on the periphery of dendrimers (Scheme 1).…”
Section: Synthesis Of Fitc Labelled Dendrimers and Dendronsmentioning
confidence: 99%
“…In both cases, the synthesis was performed from compounds containing one -NH 2 group and several -NMe 2 functions, employing the typical addition of a -NH 2 moiety to the isothiocyanate function of modified FITC (5 0 -isothiocyanatefluorescein) and the quaternization with MeI of dimethylamino (-NMe 2 ) peripheral groups. The amine groups on the periphery of carbosilane dendrimers and dendrons were introduced by thiol-ene click chemistry, which is a simple procedure to achieve this goal in carbosilane dendritic molecules with high yields [57][58][59][60]. The reaction of vinyl dendrimers GnO 3 V m (n = 1, m = 6; n = 2, m = 12; n = 3, m = 24) [59] with one equivalent of cysteamine hydrochloride HS(CH 2 ) 2 NH 3 Cl, under UV irradiation, enabled the introduction of one of these functions on the periphery of dendrimers (Scheme 1).…”
Section: Synthesis Of Fitc Labelled Dendrimers and Dendronsmentioning
confidence: 99%
“…It is a thiol-ene reaction which involves the reaction of a S-H with a double bond. Thiol-ene reactions are efficient since it produces high yields and the resulting chemical bond is stable in various solvents [26]. Fig.…”
Section: Chemical Reaction Backgroundmentioning
confidence: 99%
“…Для снижения энергии активации в Альдер-еновых реакциях можно использовать катализаторы нукле-офильного присоединения, например, кислоты Лью-иса, метилбензоилпероксид и т. д. Так, в [12] рассмо-трены следующие 3 модели катализаторов: CpRuCl, CpRu(H 2 O) + и CpRu + , -где Cp -циклопентен, Ru -рутений. Указано, что согласно расчетам энергии актива-ции реакций, наиболее предпочтительным катализато-ром является CpRu(H 2 O) + .…”
Section: рис 2 реакции дильса-альдера на примере взаимодействия бутunclassified