Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type Reactions

Jiang, Gaoxi; Chen, Jian; Huang, Jie‐Sheng; Che, Chi‐Ming

doi:10.1021/ol9018166

Cited by 263 publications

(128 citation statements)

References 49 publications

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“…In the case of secondary amines, there is an example with the dehydrogenation of N-neopentylallylic amine using TPP as photocatalyst to obtain the corresponding imine product [92]. Moreover, Che and co-workers [93] reported the highly efficient photooxidation of secondary benzylamines to imines in 90% yield using molecular oxygen and TPP as photosensitizer. They used directly the in situ formed imine products for further functionalization to develop an oxidative Ugi-type MCR (Scheme 24).…”

Section: Porphyrin Derivatives Acting As Photocatalystsmentioning

confidence: 52%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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Catalysis is a topic of continuous interest since it was discovered in chemistry centuries ago. Aiming at the advance of reactions for efficient processes, a number of approaches have been developed over the last 180 years, and more recently, porphyrins occupy an important role in this field. Porphyrins and metalloporphyrins are fascinating compounds which are involved in a number of synthetic transformations of great interest for industry and academy. The aim of this review is to cover the most recent progress in reactions catalysed by porphyrins in scalable procedures, thus presenting the state of the art in reactions of epoxidation, sulfoxidation, oxidation of alcohols to carbonyl compounds and C-H functionalization. In addition, the use of porphyrins as photocatalysts in continuous flow processes is covered.

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Section: Porphyrin Derivatives Acting As Photocatalystsmentioning

confidence: 52%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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“…As displayed in Figure S9 (Supporting Information), the catalytic performance of CNO sample shows no obvious change within five-cycle test, revealing its excellent stability and reusability. Besides, the selective aerobic oxidation of amines to imines, an extensively studied reaction by virtue of its chemical and biological significances, [35] was performed to investigate the catalytic activity of CNO. As shown in Table S2 (Supporting Information), CNO can effectively convert benzylamine derivatives with various substituent groups to corresponding imines with nearly 100% conversion rate and selectivity, whereas both the conversion and selectivity were found to be low for the case of pristine g-C 3 N 4 .…”

Section: Communication Inmentioning

confidence: 99%

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

et al. 2016

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Experimental data reveal that the incorporation of carbonyl groups into polymer matrix can significantly enhance singlet oxygen ((1) O2 ) generation and suppress production of other reactive oxygen species. Excitonic processes investigated by phosphorescence spectroscopy reveal enhanced triplet-exciton generation in the modified g-C3 N4 , which facilitate (1) O2 generation through an energy transfer process. Benefiting from this, the modified g-C3 N4 shows excellent conversion and selectivity in organic synthesis.

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“…[18,19] While a precise reaction mechanism awaits further study, a plausible catalytic cycle is depicted in Scheme 2. [20] It is proposed that molecular oxygen is first reduced to the superoxide radical anion by the Ru I /tripyridine complex. The radical anion then reacts with boronic acid to generate the intermediate A.…”

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confidence: 99%