Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

Nandi, Jyoti; Ovian, John M.; Kelly, Christopher B.; Leadbeater, Nicholas E.

doi:10.1039/c7ob02243c

Cited by 26 publications

(27 citation statements)

References 64 publications

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“…The oxidation of TEMPOH by O 2 .− restores the original state of TEMPO to complete the redox catalytic cycle. Furthermore, merging the 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate ([4‐AcNH‐TEMPO]BF 4 ) catalyst with the [Ru(bpy) 3 ](PF 6 ) 2 PC can be used for the oxidative functionalization of alcohols and aldehydes with azoles in the presence of Na 2 S 2 O 8 , a next step for the oxidation of alcohols …”

Section: Integrating Tempo and Its Analogues With Metal‐complex Photomentioning

confidence: 83%

“…Furthermore, merging the 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate ([4-AcNH-TEMPO]BF 4 )c atalyst with the [Ru(bpy) 3 ](PF 6 ) 2 PC can be used for the oxidative functionalization of alcohols and aldehydes with azoles in the presence of Na 2 S 2 O 8 ,anext step forthe oxidationo fa lcohols. [26] The oxidationo fa lcohols to aldehydes with quinone as a terminal oxidant facilitated by cooperative TEMPO and zinc porphyrin photocatalysis can be conducted under l > 500 nm visible-light irradiation. [27] The proposed mechanism is shown in Scheme 7.…”

Section: Integrating Tempo and Its Analogues With Metal-complex Photomentioning

confidence: 99%

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Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Lang

Zhao

2018

Chemistry An Asian Journal

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Visible light has risen to become a very important facilitator for selective radical reactions enabled by well-cognized photocatalysts. The renaissance of visible-light photocatalysis on this matter partly relies on integrating it with other fields of catalysis. In parallel, 2,2,6,6-tetramethylpiperidin N-oxide (TEMPO), a quintessential persistent radical, has a wide range of uses owing to its exceptional redox behavior, which gives rise to its latest prominence in catalysis. Therefore, integrating the catalysis of TEMPO with photocatalysis to perform visible-light-induced selective reactions becomes a very convenient marriage of merits. In this context, the integration of different types of photocatalysts, including metal complexes, metal-free organic dyes, and semiconductors, with TEMPO for outstanding organic transformations will be summarized. To expand further the catalytic repertoire, the integration of TEMPOH analogues such as NHPI (N-hydroxyphthalimide) and NHS (N-hydroxysuccinimide) with photocatalysis will also be discussed. Hopefully, these advances will pave the way for more breakthroughs by integrating TEMPO and its analogues with photocatalysis to lead to a valuable blueprint for visible-light-induced selective organic transformations.

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Section: Integrating Tempo and Its Analogues With Metal‐complex Photomentioning

confidence: 83%

Section: Integrating Tempo and Its Analogues With Metal-complex Photomentioning

confidence: 99%

Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Lang

Zhao

2018

Chemistry An Asian Journal

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“…And 4‐substituted derivatives of TEMPO show only comparable conversions and improvement of selectivities cannot be observed in the present study (entries 2–7, Table ). Notably, CH 3 CONH‐TEMPO was reported as an efficient co‐catalyst for oxidation of alcohols in catalytic systems or oxidative functionalization of alcohols in photocatalytic system . However, the activity CH 3 CONH‐TEMPO (entry 6, Table ) was only comparable with that of TEMPO.…”

Section: Resultsmentioning

confidence: 99%

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

et al. 2018

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Visible light‐driven interfacial redox reactions during dye‐sensitized TiO2 are essential to meet the energy and environmental challenges in the form of dye‐sensitized solar cells and sensitized degradation of organic pollutants. Inspired by these prior successes, it is conceivable that the underlying principles of these processes can guide us to construct selective chemical transformations in which the control of selectivity is in higher demand. We attempt to improve the selectivity for sulfoxides during the visible light‐driven selective aerobic oxidation of sulfides in the merger of dye‐sensitized TiO2 photocatalysis with TEMPO [(2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl] catalysis. Thus, different factors like the TEMPO and its derivatives, initial O2 pressures, initial sulfide concentrations, solvents, light‐emitting diodes (LED) and TiO2 were examined to identify the critical factor for selectivity improvement. It was found that an easily synthesized anatase TiO2, sensitized by 0.33 mol % of alizarin red S, was significant in improving the selectivity for sulfoxides at high conversions of sulfides with the aid of 2 mol % of TEMPO as a redox mediator under blue LED irradiation. This work suggests that the engineering of the TiO2 materials can be a viable solution in improving the selectivity of visible light‐driven chemical transformations by dye‐sensitized TiO2 photocatalysis.

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“…Nandi et al. developed a ruthenium‐catalyzed, oxoammonium‐mediated oxidative strategy for the amidation of aldehydes with pyrazole (Scheme a) . This strategy could be performed in the presence of [Ru(bpy) 3 (PF 6 ) 2 ] as a catalyst and ACT as an oxidant, sodium persulfate as a secondary oxidant, and pyridine in MeCN at room temperature for 24 h. A variety of aromatic aldehydes and aliphatic aldehydes were found to be active in this oxidative process.…”

Section: Synthesis Of Amides From Aldehydesmentioning

confidence: 99%

Carbonyl Compounds′ Journey to Amide Bond Formation

Reddy

Beatriz

Lima

2019

Chemistry An Asian Journal

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The formation of amide bonds is one of the most stimulating emerging areas in organic and medicinal chemistry.A mides are recognized as central building blocks in a plethora of interesting pharmaceuticals, proteins, peptides, polymers, naturalp roducts, functional materials, andb iologically relevant carbocyclic or heterocyclic molecules, and they are also found in av ariety of industrial fields. Therefore, a review of recent developments and challenges in the formation of amide bonds from carbonyl compounds is particular-ly important. Herein, we have scrutinized ar ange of metalcatalyzed andm etal-free approaches for the synthesis of amides from aldehydes, ketones, and oximes. In addition, this Minireview highlightsr elevant mechanistic studies, as well as the potential applications of these methods in the synthesis of candidate drug molecules. We hope that the data compiled herein will encourage further progress in this notable area of chemistry research.

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Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

Cited by 26 publications

References 64 publications

Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

Carbonyl Compounds′ Journey to Amide Bond Formation

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Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

Cited by 26 publications

References 64 publications

Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Integrating TEMPO and Its Analogues with Visible‐Light Photocatalysis

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO2

Carbonyl Compounds′ Journey to Amide Bond Formation

Contact Info

Product

Resources

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Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂