Dual catalysis: combining photoredox and Lewis base catalysis for direct Mannich reactions

Rueping, Magnus; Vila, Carlos; Koenigs, René M.; Poscharny, Konstantin; Fabry, David C.

doi:10.1039/c0cc04539j

Cited by 374 publications

(136 citation statements)

References 56 publications

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“…The reaction proceeds in high chemical yields by using Ir III catalyst without the need for an external oxidant. Rueping et al [7] combined photoredox catalysis and Lewis base catalysis to develop a dual catalytic system for the Mannich reaction. The two successful cases of CDC and Mannich reactions indicate that the visible-light-induced catalysis is an interesting subject even though the high cost and potential toxicity of Ru II and Ir III complexes as well as their limited availability are disadvantages of the metal-based methods.…”

Section: Introductionmentioning

confidence: 99%

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Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Liu

Zhang

et al. 2011

Chemistry A European J

266

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With visible-light irradiation, a mild, simple, and efficient metal-free photocatalytic system for the facile construction of sp(3)-sp(3) C-C bonds between tertiary amines and activated C-H bonds has been achieved. Spectroscopic study and product analysis demonstrate for the first time that photoinduced electron transfer from N-aryl tetrahydroisoquinolines to eosin Y bis(tetrabutylammonium salt) (TBA-eosin Y) takes place to generate TBA-eosin Y radical anion, which can subsequently react with nucleophiles and molecular oxygen. More strikingly, electron spin resonance (ESR) measurements provide direct evidence for the formation of superoxide radical anions (O(2)(-.)) rather than singlet oxygen ((1)O(2)) during visible-light irradiation. This active species is therefore believed to be responsible for the large rate of acceleration of the aerobic photocatalytic reactions.

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Section: Introductionmentioning

confidence: 99%

“…Despite the fact that the yields are modest, the present system being performed by pure organocatalysts adds significantly to previous methodologies. [7,19] …”

mentioning

confidence: 98%

Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Liu

Zhang

et al. 2011

Chemistry A European J

266

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“…68 ) leads to the alcohol activation (Scheme 57). As compared to the original Appel reaction 74 , this photocatalytic version is substantially more atom-economic obviating the use of stoichiometric triphenylphosphine reductant and avoiding disposal of its unpleasant oxidation product triphenylphospine oxide.…”

Section: Scheme 56mentioning

confidence: 99%

Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots

Teplý

2011

Collect. Czech. Chem. Commun.

464

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Reactions triggered by light constitute a treasure trove of unique synthetic methods that are available to chemists. Photoinduced redox processes using visible light in conjunction with sensitizing dyes offer a great variety of catalytic transformations useful in the realm of organic synthesis. The recent literature amply shows that this preparative toolbox is expanding substantially. This review discusses historical and contemporary work in the area of photoredox catalysis with [Ru(bpy)3]2+. Elegant examples from the most recent literature document the importance of this fast developing area of research. The photoredox chemistry has also emerged as a promising bond-making and bond-breaking tool for chemical biology and materials chemistry. A review with 96 references.

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“…Weitere einzelne Beispiele, bei denen ein photochemisch erzeugtes Dihydroisochinoliniumion enantioselektiv mit einem Nukleophil in einer dualen Katalyse umgesetzt wurde, wurden für eine Mannich-Reaktion [111] und eine Aza-BaylisHillman-Reaktion [112] beschrieben.…”

Section: Kationen Als Gegenionenunclassified

Enantioselektive Katalyse photochemischer Reaktionen

et al. 2015

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Die Natur des angeregten Zustands macht die Entwicklung chiraler Katalysatoren für enantioselektive photochemische Reaktionen zu einer enormen Herausforderung. Die Absorption eines 400‐nm‐Photons entspricht einer Energieaufnahme von etwa 300 kJ mol−1. Es bedarf innovativer Konzepte, um in einem derart großen Abstand vom Grundzustand Reaktionspfade zu eröffnen, die gezielt zu einem Enantiomer einer chiralen Verbindung führen. Hier werden die beiden wesentlichen Vorgehensweisen für homogen katalysierte, enantioselektive Prozesse diskutiert. Im ersten Teil werden chirale Photokatalysatoren besprochen, die in den photochemischen Schlüsselschritt eingreifen und in diesem Schritt eine asymmetrische Induktion bewirken. Im zweiten Teil werden Reaktionen vorgestellt, in denen die photochemische Anregung durch einen achiralen Katalysator erfolgt und die asymmetrische Induktion durch einen zweiten chiralen Katalysator gewährleistet wird (duale Katalyse).

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Dual catalysis: combining photoredox and Lewis base catalysis for direct Mannich reactions

Cited by 374 publications

References 56 publications

Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots

Enantioselektive Katalyse photochemischer Reaktionen

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