Probleme und Möglichkeiten der radikalischen Addition von Thiolen an ungesättigte Verbindungen

Griesbaum, Karl

doi:10.1002/ange.19700820703

Cited by 88 publications

(39 citation statements)

References 61 publications

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“…Precisely tailored mf-PEGs are most effectively obtained if reactions exhibiting very high yields, high selectivity, versatility, and simplicity-in recent years designated "click reactions"-are applied. [102][103][104][105][106][107][108][109] The transformation of copolymers of EO and allyl glycidyl ether (AGE) through thiol-ene coupling (TEC) [110][111][112][113] represents a powerful modular platform for precisely tailored mf-PEGs. [58,[76][77][78][79][80][81][82][83][84][85] Through commercial AGE as a comonomer, an adjustable number of allyl ethers can be introduced at the PEG backbone (in a random or block fashion), which are accessible for TEC.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Multifunctional Poly(ethylene glycol)s

et al. 2011

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In the rapidly evolving multidisciplinary field of polymer therapeutics, tailored polymer structures represent the key constituent to explore and harvest the potential of bioactive macromolecular hybrid structures. In light of the recent developments for anticancer drug conjugates, multifunctional polymers are becoming ever more relevant as drug carriers. However, the potentially best suited polymer, poly(ethylene glycol) (PEG), is unfavorable owing to its limited functionality. Therefore, multifunctional linear copolymers (mf-PEGs) based on ethylene oxide (EO) and appropriate epoxide comonomers are attracting increased attention. Precisely engineered via living anionic polymerization and defined with state-of-the-art characterization techniques-for example real-time (1)H NMR spectroscopy monitoring of the EO polymerization kinetics-this emerging class of polymers embodies a powerful platform for bio- and drug conjugation.

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Section: Synthetic Strategiesmentioning

confidence: 99%

Multifunctional Poly(ethylene glycol)s

et al. 2011

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“…Hence our method is essentially based on the alkene hydrothiolation reaction, the so called thiol-ene coupling (TEC), that being thermally or photochemically induced occurs by a radical mechanism in anti-Markovnikov regioselective fashion (Scheme 1). [14] The great potential of this high yielding reaction that is not metal-based catalyst dependent and is compatible with oxygen and water has been amply documented in polymer chemistry and to a lesser extent in bioorganic chemistry. [15] The potential role of this reaction in carbohydrate and protein chemistry has been validated, however, by significant applications such as heteroglycoclusters, [16] vaccines, [17] and S-disaccharides [18] syntheses as well as by the site-specific immobilization and patterning of proteins.…”

mentioning

confidence: 99%

A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol–Ene Coupling

Dondoni

Massi

Nanni

et al. 2009

Chemistry A European J

133

102

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“…[38] The opposite regioselectivity of addition occurred in the absence of a catalyst, and linear, antiMarkovnikov products 53 were formed through a radical reaction (Scheme 15 A). [39] "Hidden Brønsted acid" catalysis was discounted, as both triflic and triflimidic acid gave only low yields of Markovnikov product 52, along with high yields of anti-Markovnikov product 53 arising from the uncatalysed radical addition. Interestingly, if FeCl 3 was used alone, low yields of both products were obtained, with excellent recovery of the starting material, suggesting the presence of iron may inhibit the radical addition mechanism.…”

Section: (No)]mentioning

confidence: 99%

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

2014

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The metal‐catalysed hydrofunctionalisation of alkenes and alkynes provides a convenient and atom‐economic route to diversely functionalised products with control of regio‐, chemo‐ and stereoselectivity. As one of the most abundant elements on earth, iron offers a level of sustainable and long‐term availability that is uncommon for most transition metals. Although iron is commonly found in the oxidation states of +2 and +3, the use of redox‐active ligands has allowed the synthesis and application of low oxidation state iron complexes in catalysis. A broad range of hydrofunctionalisation reactions have been developed by using iron catalysts in a wide variety of oxidation states. Intense development over the past decade has resulted in the development of iron‐catalysed hydroamination, hydroalkoxylation, hydrocarboxylation, hydrothiolation, hydrovinylation, hydrosilylation, hydroboration, hydrophosphination, hydromagnesiation and carbonylation reactions, amongst others. With the field still in its infancy, there is great potential for further developments in the mechanistic understanding and synthetic and industrial applicability of these processes.

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Probleme und Möglichkeiten der radikalischen Addition von Thiolen an ungesättigte Verbindungen

Cited by 88 publications

References 61 publications

Multifunctional Poly(ethylene glycol)s

Multifunctional Poly(ethylene glycol)s

A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol–Ene Coupling

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

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