Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C–H homocoupling of quinoline N-oxides

Stephens, David E.; Lakey-Beitia, Johant; Chavez, Gabriel; Ilie, Carla; Arman, Hadi D.; Larionov, Oleg V.

doi:10.1039/c5cc02227d

Cited by 63 publications

(36 citation statements)

References 42 publications

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“…This result demonstrated the preference of electron‐withdrawing iodonium salt over the electron‐rich one because herein electron‐withdrawing groups enhance the electrophilicity of the aryl group. Then stoichiometric reaction of Pd(OAc) 2 with substrate 1 a in the absence of arylating agent led to the formation of complexes A – C which substantiated the formation of five membered cyclopalladacycle intermediate as demonstrated by Larionov and his co‐workers (Scheme c) . Although none of the complexes A – C was isolated or observed by 1H NMR, however their formation was confirmed by HRMS (for detail refer ESI).…”

Section: Resultssupporting

confidence: 63%

Palladium‐Catalyzed Regioselective C−H Arylation of Quinoline‐N‐Oxides at C‐8 Position using Diaryliodonium Salts

2020

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A simple and efficient Pd(II)‐catalyzed site‐selective direct arylation strategy was demonstrated for the synthesis of 8‐arylquinoline‐N‐oxide derivatives using quinoline‐N‐oxides and (aryl)(mesityl)iodonium triflates. A series of control experiments were carried out to elucidate the reaction mechanism. The synthetic potential was extended with the C‐2 post‐modification of the final derivative.

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Section: Resultssupporting

confidence: 63%

Palladium‐Catalyzed Regioselective C−H Arylation of Quinoline‐N‐Oxides at C‐8 Position using Diaryliodonium Salts

2020

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“…[175] Another potential mode of action may involve complexation of metal ions by the oxygen atom of heterocyclic N -oxides. [176] These potential modes of action in addition to the known ones, and in conjunction with the ease of synthesis [177] and rapid structural diversification [178] of the heterocyclic N -oxide scaffold make it a very promising structural motif for drug discovery. It is expected that the review will attract further attention to this topic and lead to the discovery of new potent medicinal N -oxide heterocycles.…”

Section: Discussionmentioning

confidence: 99%

Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents

Mfuh¹,

Larionov

2015

CMC

135

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Heterocyclic N-oxides have emerged as potent compounds with anticancer, antibacterial, antihypertensive, antiparasitic, anti-HIV, anti-inflammatory, herbicidal, neuroprotective, and procognitive activities. The N-oxide motif has been successfully employed in a number of recent drug development projects. This review surveys the emergence of this scaffold in the mainstream medicinal chemistry with a focus on the discovery of the heterocyclic N-oxide drugs, N-oxide-specific mechanisms of action, drug-receptor interactions and synthetic avenues to these compounds. As the first review on this subject that covers the developments since 1950s to date, it is expected that it will inspire wider implementation of the heterocyclic N-oxide motif in the rational design of new medicinal agents.

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“…130 During optimization of their Pd-catalyzed C8-site-selective arylation, 128 a formation of a side product was observed in some instances. Upon removal of the iodoarene from the reaction mixture, the yield of the side product increased to almost 50%.…”

Section: C8–h-functionalizationmentioning

confidence: 99%

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

2015

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This review summarizes recent developments in the C–H-functionalization of the distal positions of pyridines, quinolines and related azaheterocycles. While the functionalization of the C2 position has been known for a long time and is facilitated by the proximity to N1, regioselective reactions in the distal positions are more difficult to achieve and have only emerged in the last decade. Recent advances in the transition metal-catalyzed distal C–H-functionalization of these synthetically-important azaheterocycles are discussed in detail, with the focus on the scope, site-selectivity and mechanistic aspects of the reactions.

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Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C–H homocoupling of quinoline N-oxides

Cited by 63 publications

References 42 publications

Palladium‐Catalyzed Regioselective C−H Arylation of Quinoline‐N‐Oxides at C‐8 Position using Diaryliodonium Salts

Palladium‐Catalyzed Regioselective C−H Arylation of Quinoline‐N‐Oxides at C‐8 Position using Diaryliodonium Salts

Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

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