Synthesis of Acridinium Photocatalysts via Site-Selective C–H Alkylation

Yan, Hong; Song, Jinshuai; Zhu, Shaobin; Xu, Hai‐Chao

doi:10.31635/ccschem.021.202000743

Cited by 50 publications

(44 citation statements)

References 45 publications

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“…These features ensure efficient mass transfer, facilitates conversion, allow easy scale‐up, and reduce the use of supporting electrolyte [53–58] . Despite these attractive features of continuous flow electrochemistry, its synthetic applications remain scarce [47,59–65] …”

Section: Direct Electrolysismentioning

confidence: 99%

Electrochemically Driven Radical Reactions: From Direct Electrolysis to Molecular Catalysis

Chen

2021

The Chemical Record

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Organic radicals are versatile synthetic intermediates that provide reactivities and selectivities complementary to ionic species. Despite its long history, electrochemically driven radical reactions remain limited in scope. In the past few years, there have been dramatic increase in research activity in organic electrochemistry. We have been developing electrochemical and electrophotocatalytic methods for the generation and synthetic utilization of organic radicals. In our studies, various radical species such as alkene and arene radical cations and carbon‐ and heteroatom‐centered radicals are generated from readily available precursors through direct electrolysis, molecular electrocatalysis or molecular electrophotocatalysis. These radical species undergo various inter‐ and intramolecular oxidative transformations to rapidly increase molecular complexity. The simultaneous occurrence of anodic oxidation and cathodic proton reduction allows the oxidative reactions to proceed through H2 evolution without external chemical oxidants.

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Section: Direct Electrolysismentioning

confidence: 99%

Electrochemically Driven Radical Reactions: From Direct Electrolysis to Molecular Catalysis

Chen

2021

The Chemical Record

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“…Ar Very recently, the Xu group reported a new way to combine photocatalysis and electrochemistry (Figure 30). 117 In a batch or flow process, acridinium substrates 30-1 react with an alkyl potassium tetrafluoroborate under irradiation with a blue LED to give monoalkylated intermediates 30-3. These intermediates undergo an electrochemical rearomatization reaction in one pot or in a flow apparatus.…”

Section: Page 33 Of 60 Ccs Chemistrymentioning

confidence: 99%

Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis

et al. 2022

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“…Skalierbare Synthese von Acridiniumsalzen : Die Xu‐Gruppe stellte außerdem eine Bibliothek an 3/6‐substituierten Acridinium‐PRC‐Katalysatoren aus einem Acridinium‐Kern 60 unter Verwendung von Trifluoroboratsalzen her (Abbildung 28 A). [57d,e] Die Reaktionen wurden iterativ durchgeführt, um monosubstituierte 61 (74–97 %, Abbildung 28 B) oder bisubstituierte Katalysatoren 62 / 63 (31–83 %, Abbildung 28 C) zu erhalten. Beeindruckend ist, dass in jedem Schritt verschiedene Trifluoroboratsalze verwendet werden können, wodurch unsymmetrische 3,6‐disubstituierte Acridiniumsalze erhalten werden.…”

Section: Photokatalysator‐elektrorecyclingunclassified

Synthetische molekulare Photoelektrochemie: neue synthetische Anwendungen, mechanistische Einblicke und Möglichkeiten zur Skalierung

Kaur

Karl

et al. 2022

Angewandte Chemie

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Die synthetische Photoelektrochemie (PEC) bietet neue Möglichkeiten für die Erzeugung und Handhabung reaktiver Zwischenstufen. Selektive Einelektronentransferreaktionen (SET) auf wesentlich umweltfreundlichere Weise und die Erweiterung des Redoxfensters erwecken Aufmerksamkeit. Dieser Aufsatz befasst sich mit den diesbezüglich neusten Beiträgen. Besprochen werden die Kombination von PEC mit anderen Reaktivitäten (Wasserstoffatomtransfer, radical–polar crossover, Energietransfer‐Sensibilisierung), die Skalierbarkeit bis zum Multigramm‐Maßstab, neuartige Selektivitäten bei SET‐Superoxidationen/Reduktionen und die Bedeutung der Vorkomplexierung, um die Katalyse angeregter Radikalionen zeitlich zu ermöglichen.

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Synthesis of Acridinium Photocatalysts via Site-Selective C–H Alkylation

Cited by 50 publications

References 45 publications

Electrochemically Driven Radical Reactions: From Direct Electrolysis to Molecular Catalysis

Electrochemically Driven Radical Reactions: From Direct Electrolysis to Molecular Catalysis

Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis

Synthetische molekulare Photoelektrochemie: neue synthetische Anwendungen, mechanistische Einblicke und Möglichkeiten zur Skalierung

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