Visible Light Assisted Photocatalytic [3 + 2] Azide–Alkyne “Click” Reaction for the Synthesis of 1,4-Substituted 1,2,3-Triazoles Using a Novel Bimetallic Ru–Mn Complex

Kumar, Pawan; Joshi, Chetan; Srivastava, Ambrish Kumar; Gupta, Prasoon; Boukherroub, Rabah; Jain, Suman L.

doi:10.1021/acssuschemeng.5b00653

Cited by 57 publications

(31 citation statements)

References 41 publications

(69 reference statements)

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“…Again, solvent-less microwave irradiation technique was also been reported for a 1,3-dipolar cycloaddition reaction between terminal alkynes and azides to synthesize 1,2,3-triazoles using polymer supported copper(I) composite, fabricated using a one-step chemical synthesis route under ambient condition 26 . Protocols have also been reported for the photoinduced formation of Cu(I) using graphitic carbon nitride 27 , fullerene 28 and bimetallic complex comprising a photosensitizer ruthenium unit 29 as a photocatalyst, from the Cu (II) precursor in the presence of amine as a base molecule for azide-alkyne cycloaddition reaction.…”

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confidence: 99%

Light effect on Click reaction: Role of photonic quantum dot catalyst

Nandi

Taher

Islam

et al. 2016

Sci Rep

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Due to the light excitation, the valence band electron of the copper (I) sulfide quantum dot transfer to the conduction band and act as a scavenger of the terminal proton of the alkyne in the presence of organic azide with the formation of 1,4-disubstituted 1,2,3-triazoles, where the copper(I) species of Cu2S act as a catalyst for the reaction. The above cycloaddition reaction between alkyne and azide is commonly known as the Click reaction. In this study, experiments were carried out under the exposure of ultra-violate and daylight and also dark environment. According to the original recommendation for the Click reaction, the role of the base was also considered for this experiment. We found that the effect of conduction band electron is more efficient than the recommended conventional base mediated reaction procedure.

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confidence: 99%

Light effect on Click reaction: Role of photonic quantum dot catalyst

Nandi

Taher

Islam

et al. 2016

Sci Rep

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“…[229] Dieser Aktivierungsmodus kann auch durch Photokatalyse mit sichtbarem Licht unter Verwendung von Flavin [230] oder dem bimetallischen Ru/Mn-Komplex 237 erreicht werden, der in Gegenwart eines Opferelektronendonors (Triethylamin, NEt 3 )e in Elektron effizient auf Cu II -Sulfat überträgt und die katalytisch aktive Cu I -Spezies bildet (Schema 66 d, rechts). [231]…”

Section: Angewandte Chemieunclassified

Photokatalyse mit sichtbarem Licht: Welche Bedeutung hat sie für die organische Synthese?

et al. 2018

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Die Photokatalyse mit sichtbarem Licht hat sich im letzten Jahrzehnt zu einer breit angewandten Methode in der organischen Synthese entwickelt. Für viele wichtige Reaktionen, wie Kreuzkupplungen, α‐Amino‐Funktionalisierungen, Cycloadditionen, ATRA‐Reaktionen oder Fluorierungen, wurden photokatalytische Varianten berichtet. Um Chemiker bei der Auswahl photokatalytischer Methoden für ihre Synthesen zu unterstützen, vergleichen wir in diesem Aufsatz klassische und photokatalytische Verfahren für ausgewählte Reaktionsklassen und zeigen deren Vorteile und Grenzen auf. In vielen Fällen verlaufen die photokatalytischen Reaktionen unter milderen Reaktionsbedingungen, typischerweise bei Raumtemperatur, und stöchiometrische Reagenzien werden durch einfache Oxidanzien oder Reduktionsmittel wie Luft, Sauerstoff oder Amine ersetzt. Beeinflusst die Photokatalyse mit sichtbarem Licht die organische Synthese? Die Aussicht, Elektronen zu Substraten und Zwischenprodukten hin‐ und herzuschieben oder Energie selektiv durch einen sichtbares Licht absorbierenden Photokatalysatoren zu übertragen, verspricht die aktuellen Verfahren in der Radikalchemie zu verbessern und neue Wege durch den Zugang zu reaktiven, bisher unbekannten Spezies zu erschließen, insbesondere durch das Zusammenspiel von Photokatalyse mit der Organo‐ oder Metallkatalyse.

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“…Because of the higher photoredox potential in comparison to that the corresponding [Ru(bpy) 3 ] 2+ , cyclometalated Ir(III) complexes are frequently used as photoredox catalysts in organic transformations . Various bimetallic Ru(II)–M complexes bridged by bpm have been prepared, and their structures and properties have been investigated . However, there are only a few reports on bpm‐bridged bimetallic Ru(II)–Ir(III) complexes .…”

Section: Introductionmentioning

confidence: 99%

Bimetallic Ru(II)–Ir(III) complexes with bridging 2,2′‐bipyrimidine: Synthesis, structures and characterization

Zhang

Liu

2018

J Chinese Chemical Soc

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In this work, four bimetallic Ru(II)-Ir(III) complexes with the general formula [(bpy) 2 Ru(bpm)Ir(C^N) 2 ](PF 6 ) 3 (bpy = 2,2-bipyridine, bpm = 2,2 0 -bipyrimidine, C^N = 2-phenylpyridinato (2), (2-p-tolyl)pyridinato (3), 2-(2,4-difluorophenyl) pyridinato (4), and 2-thienylpyridinato (5)) were synthesized. Complexes 2-5 were characterized by NMR spectroscopy, high-resolution mass spectrometry, and elemental analysis. The structures of the complexes 2 and 4 were further confirmed by single-crystal X-ray diffraction analysis. All the complexes display strong absorption in the high-energy UV region assigned to intraligand (IL) transitions, and the lower energy bands are ascribed to metal-to-ligand charge transfer (MLCT) transitions. The reduction and oxidation behavior of the complexes 2-5 were examined by cyclic voltammetry. Variation of the ligands on Ir(III) center resulted in significant changes in electrochemical properties.2,2 0 -bipyrimidine, bimetallic complex, electrochemistry, photophysical property, X-Ray structure

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Visible Light Assisted Photocatalytic [3 + 2] Azide–Alkyne “Click” Reaction for the Synthesis of 1,4-Substituted 1,2,3-Triazoles Using a Novel Bimetallic Ru–Mn Complex

Cited by 57 publications

References 41 publications

Light effect on Click reaction: Role of photonic quantum dot catalyst

Light effect on Click reaction: Role of photonic quantum dot catalyst

Photokatalyse mit sichtbarem Licht: Welche Bedeutung hat sie für die organische Synthese?

Bimetallic Ru(II)–Ir(III) complexes with bridging 2,2′‐bipyrimidine: Synthesis, structures and characterization

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