Polar effects in free-radical reactions. Carbamoylation and .alpha.-N-amidoalkylation of heteroaromatic bases by amides and hydroxylamine-O-sulfonic acid

Citterio, Attilio; Gentile, Anna; Minisci, Francesco; Serravalle, Marco; Ventura, Susanna

doi:10.1021/jo00192a022

Cited by 34 publications

(13 citation statements)

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“…Thus, 4-ethyl pyridine provided a mixture of 4ethyl-N,N-dimethylpicolinamide and N-((4-ethylpyridin-2-yl)methyl)-N-methylformamide in yields and ratios depending on the oxidant (Scheme 38a). This seminal report was followed by intensive studies on the radical fragmentation of DM by Minisci and co-workers [116][117][118]. Then, the promotion of such reactions under sunlight, especially in the presence of TiO2, was disclosed by Caronna and co-workers (Scheme 38b) [119].…”

Section: Rc=on(ch2)me Fragmentmentioning

confidence: 97%

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Мuzart¹

2021

Molecules

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Section: Rc=on(ch2)me Fragmentmentioning

confidence: 97%

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Мuzart¹

2021

Molecules

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“…In particular, they considered the amidation of lepidine and quinoxaline to the corresponding products 36 and 37, respectively, and compared the photochemical approach (Scheme 25(a)) with the thermal one reported by Citterio et al consisting in the use of HSA and Fe(II) salt in formamide water (10/1) solutions of the heteroaromatic bases (Scheme 25(b)) [43]. SCHEME 23 Acylation versus alkylation.…”

Section: Is It a Green Approach?mentioning

confidence: 99%

Photocatalytic Minisci Reaction

Gambarotti¹,

Melone²,

Punta³

et al. 2015

Green Synthetic Approaches for Biologically Relevant Heterocycles

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“…Formamides and N,N-alkylformamides are well known substrates suitable as nuchleophylic radical sources [45]. In the presence of TiO 2 /H 2 O 2 /sunlight system, amides give the corresponding carbon centered radicals which add to protonated heterocyclic bases.…”

Section: Carbamoylation Of Heterocyclic Bases In the Presence Of H 2 mentioning

confidence: 99%

TiO2 in Organic Photosynthesis: Sunlight Induced Functionalization of Heterocyclic Bases

Gambarotti¹,

Punta²,

Recupero³

et al. 2010

COC

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In the last decades photocatalyzed organic processes have attracted the great interest, due to their low environmental impact. Various oxidation and reduction processes of organic substrates have been developed as alternative routes to the "classical" synthesis of more complex molecules. In this attempt TiO2 is actually largely studied and employed, especially as catalyst in the organic pollutants photodegradation to products with less environmental impact. From the synthetic point of view, the attention has been focused particularly on the TiO2-mediated synthesis of alcohols, carbonyl-and carboxylic-derivatives. Recently our group has developed new TiO2-photocatalyzed synthetic protocols for the functionalization of N-heteroaromatic bases as an alternative to the "classic" well known redox metal-catalyzed methods. These substrates are suitable for the nucleophilic free-radical addition and the photocatalytic activity of microcrystalline TiO2 has shown a key role in the success of our protocol.

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Polar effects in free-radical reactions. Carbamoylation and .alpha.-N-amidoalkylation of heteroaromatic bases by amides and hydroxylamine-O-sulfonic acid

Cited by 34 publications

References 0 publications

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Photocatalytic Minisci Reaction

TiO2 in Organic Photosynthesis: Sunlight Induced Functionalization of Heterocyclic Bases

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