Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines

Chen, Jianqiang; Yu, Wancong; Wei, Yuanyuan; Li, Tenghui; Xu, Peng‐Fei

doi:10.1021/acs.joc.6b02377

Cited by 69 publications

(29 citation statements)

References 62 publications

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“…In 2017, Chen et al developed a visible light photoredox-induced three-component cascade reaction to synthesize 2-imidazoline (355) (Scheme 99). [96] The reaction utilized olefins (352), N-protected 1-aminopyridinium tetrafluoroborate salts (353), and nitriles (354) in the presence of photocatalyst (Ir(ppy) 3 ) and blue LED light source. Treatment of various aromatic and aliphatic substituted olefins with the 1-aminopyridinium salts (353) and aliphatic nitriles (354) afforded the imidazoline analogs in moderate to good yields (71-97%).…”

Section: Methods F: Synthesis Of Imidazolines From Cyanidesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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Imidazoline is an important class of compounds found in numerous natural and pharmaceutical products. The compounds are also used as an intermediate in the synthesis of organic molecules. Moreover, chiral imidazolines are widely utilized as organocatalysts to synthesize various natural and synthetic organic compounds. In the past decade, there was an increase in interest in developing new methods to synthesize these imidazoline analogs. Both modification of the previously established methods and the development of new methods are carried out significantly. This review article highlights the progress of the synthesis of imidazoline scaffolds in the last few years (2009-present). The review also described the proposed mechanism illustrated in many of the reports.

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Section: Methods F: Synthesis Of Imidazolines From Cyanidesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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“…[63] Alternatively,X ua nd co-workers found that, in the absence of as uitable nucleophile to trap the cationic intermediate,the use of acetone or acetonitrile as the solvent enables the synthesis of substituted imidazolines 19 and oxazolidines 20,r espectively (Scheme 14). [64] When inert, non-nucleophilic solvents such as dichloromethane are employed, intramolecular reaction of the amine with the transiently generated cation yields valuable aziridine products 21. [65,66] Later studies by the same group also established that the use of dichloromethane as the solvent furthermore enables the use of weak nucleophiles such as fluoride or chloride to afford aminofluorinated and chlorinated products, respectively.…”

Section: Reviewsmentioning

confidence: 99%

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

et al. 2020

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In this Review, we highlight recent advances in the understanding and design of N‐functionalized pyridinium scaffolds as redox‐active, single‐electron, functional group transfer reagents. We provide a selection of representative methods that demonstrate reactivity and fundamental advances in this emerging field. The reactivity of these reagents can be divided into two divergent pathways: homolytic fragmentation to liberate the N‐bound substituent as the corresponding radical or an alternative heterolytic fragmentation that liberates an N‐centered pyridinium radical. A short description of the elementary steps involved in fragmentation induced by single‐electron transfer is also critically discussed to guide readers towards fundamental processes thought to occur under these conditions.

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“…Des Weiteren fanden Xu und Mitarbeiter heraus, dass in Abwesenheit eines geeigneten Nukleophils, um das kationische Zwischenprodukt abzufangen, die Verwendung von Aceton oder Acetonitril als Lösungsmittel die Synthese von substituierten Imidazolinen 19 bzw. Oxazolidinen 20 ermöglicht (Schema ) . Bei Verwendung von inerten, nicht nukleophilen Lösungsmitteln wie Dichlormethan ergibt die intramolekulare Reaktion des Amins mit dem transient erzeugten Kation wertvolle Aziridinprodukte 21 .…”

Section: Pyridiniumsalze Als Reagenzien Zur üBertragung Funktionellerunclassified

Pyridiniumsalze als redoxaktive Reagenzien zur Übertragung funktioneller Gruppen

Rössler¹,

Jelier²,

Magnier

et al. 2020

Angewandte Chemie

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In diesem Aufsatz sind die jüngsten Fortschritte beim Verständnis und Design von N‐funktionalisierten Pyridiniumsalzen als redoxaktivierte Einelektronentransfer‐Reagenzien zur Übertragung funktioneller Gruppen zusammengefasst. Anhand einer Auswahl an repräsentativen Methoden werden Reaktivität und grundlegende Fortschritte in diesem sich rasch entwickelnden Bereich diskutiert. Diese Reagenzien weisen zwei grundsätzlich divergierende Reaktionspfade auf: homolytische Fragmentierung zur Freisetzung des N‐gebundenen Substituenten als entsprechendes Radikal oder eine alternative, heterolytische Fragmentierung zur Freisetzung eines radikalischen Pyridiniumkations. Die elementaren Schritte der durch Einelektronentransfer induzierten Fragmentierung werden kritisch diskutiert.

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Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines

Cited by 69 publications

References 62 publications

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

Pyridiniumsalze als redoxaktive Reagenzien zur Übertragung funktioneller Gruppen

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