Influence of anellation in N-heterocyclic carbenes: Novel quinoxaline-anellated NHCs trapped as transition metal complexes

Shanmuganathan, Saravanakumar; Kindermann, Markus; Heinicke, Joachim; Köckerling, Martin

doi:10.1039/b512884f

Cited by 86 publications

(30 citation statements)

References 38 publications

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“…[34] Adding a redox-active moiety to a NHC gives interesting properties to the resulting metal complexes. In this context, NHCs bearing a naphthoquinone 21, [35] a quinoxaline 22, [36] a ferrocene 23, [37] or a nicotinamide 24 [38] moiety have recently been reported (Scheme 10). The oxidation state of the redox-active NHCligand 21 was shown to play a critical role in the nickel(II)-catalyzed Kumada cross-coupling between PhMgCl and bromoarenes.…”

Section: Redox Active Ligandsmentioning

confidence: 99%

Redox‐Active Ligands in Catalysis

Praneeth,

Ringenberg,

Ward

2012

Angew Chem Int Ed

328

173

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Nature's use of redox-active moieties combined with 3d transition-metal ions is a powerful strategy to promote multi-electron catalytic reactions. The ability of these moieties to store redox equivalents aids metalloenzymes in promoting multi-electron reactions, avoiding high-energy intermediates. In a biomimetic spirit, chemists have recently developed approaches relying on redox-active moieties in the vicinity of metal centers to catalyze challenging transformations. This approach enables chemists to impart noble-metal character to less toxic, and cost effective 3d transitional metals, such as Fe or Cu, in multi-electron catalytic reactions.

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Section: Redox Active Ligandsmentioning

confidence: 99%

Redox‐Active Ligands in Catalysis

Praneeth,

Ringenberg,

Ward

2012

Angew Chem Int Ed

328

173

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“…Until now there is a large number of NHC frameworks known in the literature, ranging from five-membered to seven-membered rings including, imidazolium (1), imidazolinium (2, 8) [40,41], triazolium (3) [42], oxazolium (4) [43,44], thiazolium (5) [45,46], pyrrolidium (6) [47][48][49][50], benzimidazolium (7) [51,52], bisoxazoline (9) [53], quinoxaline (10a) [54], naphtha annulated imidazolium (10b) [55], diazaphosphetidin amine (11) [56], pyrimidine (12) [57,58], perimidine (13) [59], dibenzo(1,3)diazepine (14) [60], imidazopyridine (15,16) [61], 2,2′-bipyridine derived imidazolium (17) [62], bis-imidazolium with arene backbone (18) [63], etc. as shown in www.future-science.com 1307 future science group N-heterocyclic carbene metal complexes as bio-organometallic antimicrobial & anticancer drugs Review coordination properties.…”

Section: Types Of Nhcsmentioning

confidence: 99%

N -Heterocyclic Carbene Metal Complexes as Bio-Organometallic Antimicrobial and Anticancer Drugs

Patil

et al. 2015

Future Med. Chem.

149

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Late transition metal complexes that bear N-heterocyclic carbene (NHC) ligands have seen a speedy growth in their use as both, metal-based drug candidates and potentially active homogeneous catalysts in a plethora of C-C and C-N bond forming reactions. This review article focuses on the recent developments and advances in preparation and characterization of NHC-metal complexes (metal: silver, gold, copper, palladium, nickel and ruthenium) and their biomedical applications. Their design, syntheses and characterization have been reviewed and correlated to their antimicrobial and anticancer efficacies. All these initial discoveries help validate the great potential of NHC-metal derivatives as a class of effective antimicrobial and anticancer agents.

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“…[34] Das Anbinden einer redoxaktiven Einheit an ein NHC führt zu interessanten Eigenschaften des resultierenden Komplexes. In diesem Zusammenhang wurde vor kurzem über NHCs mit einem Naphthochinon-(21), [35] einem Chinoxalin-(22), [36] einem Ferrocen-(23) [37] und einem Nicotinamidrest (24) [38] …”

Section: Redoxaktive Ligandenunclassified

Redoxaktive Liganden in der Katalyse

2012

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Die in Metalloenzymen beobachtete Verwendung redoxaktiver Einheiten zusammen mit 3d‐Übergangsmetallionen ist eine leistungsfähige Strategie für katalytische Mehrelektronenreaktionen. Die redoxaktiven Einheiten in Metalloenzymen können Redoxäquivalente “speichern”, wodurch Intermediate hoher Energie vermieden werden. Chemiker haben biomimetische Strategien entwickelt, um katalytische Varianten anspruchsvoller Umwandlungen auf der Grundlage redoxaktiver Einheiten in Nachbarschaft zu Metallzentren zu entwerfen. Diese Herangehensweise bietet die Möglichkeit, wenig toxischen und kostengünstigen 3d‐Übergangsmetallen wie Fe oder Cu in katalytischen Mehrelektronenreaktionen einen Edelmetallcharakter zu verleihen.

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Influence of anellation in N-heterocyclic carbenes: Novel quinoxaline-anellated NHCs trapped as transition metal complexes

Cited by 86 publications

References 38 publications

Redox‐Active Ligands in Catalysis

Redox‐Active Ligands in Catalysis

N -Heterocyclic Carbene Metal Complexes as Bio-Organometallic Antimicrobial and Anticancer Drugs

Redoxaktive Liganden in der Katalyse

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