An Efficient Rh/O<sub>2</sub> Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen

Zhang, Guoying; Yang, Lei; Wang, Yanyu; Xie, Yinjun; Huang, Hanmin

doi:10.1021/ja404414q

Cited by 266 publications

(100 citation statements)

References 76 publications

(10 reference statements)

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“…[50] Scheme 20. Primarily,t hese catalysts have been employed in borylation reactions of unactivated arenes.Inparticular,arylboronic acid pinacol esters have been targeted due to their application in anumber of well-established diversification reactions,such as Scheme 19.…”

Section: Ir- Rh- and Ru-catalyzed C à Hb Orylation And Silylationmentioning

confidence: 99%

Increasing Catalyst Efficiency in C−H Activation Catalysis

et al. 2018

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C-H activation reactions with high catalyst turnover numbers are still very rare in the literature and 10 mol % is a common catalyst loading in this field. We offer a representative overview of efficient C-H activation catalysis to highlight this neglected aspect of catalysis development and inspire future effort towards more efficient C-H activation. Examples ranging from palladium catalysis, Cp*Rh - and Cp*Co -catalysis, the C-H borylation and silylation to methane C-H activation are presented. In these reactions, up to tens of thousands of catalyst turnovers have been observed.

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Section: Ir- Rh- and Ru-catalyzed C à Hb Orylation And Silylationmentioning

confidence: 99%

Increasing Catalyst Efficiency in C−H Activation Catalysis

et al. 2018

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“…[54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere. [54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere.…”

Section: Synthesis Of Pyridinium and Polycyclic Pyridinium Saltsmentioning

confidence: 99%

Advancements in the Synthesis and Applications of Cationic N‐Heterocycles through Transition Metal‐Catalyzed C−H Activation

Gandeepan

2015

Chemistry An Asian Journal

129

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Cationic N-heterocycles are an important class of organic compounds largely present in natural and bioactive molecules. They are widely used as fluorescent dyes for biological studies, as well as in spectroscopic and microscopic methods. These compounds are key intermediates in many natural and pharmaceutical syntheses. They are also a potential candidate for organic light-emitting diodes (OLEDs). Because of these useful applications, the development of new methods for the synthesis of cationic N-heterocycles has received a lot of attention. In particular, many C-H activation methodologies that realize high step- and atom-economies toward these compounds have been developed. In this review, recent advancements in the synthesis and applications of cationic N-heterocycles through C-H activation reactions are summarized. The new C-H activation reactions described in this review are preferred over their classical analogs.

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“…Herein, we report the synthesis of various polycyclic pyridinium salts by using substituted 2‐phenylpyridine and N(sp 2 )‐containing substrates with alkynes in good‐to‐excellent yields under very mild reaction conditions. During the preparation of this manuscript, a report has appeared on the synthesis of similar compounds 10. The reported reaction conditions required heating the reaction mixtures in MeOH at 120 °C for 22 h in the presence of O 2 and one equivalent of strong acid (HOTf) by using [RhCp*(H 2 O) 3 ] 2+ as a catalyst.…”

Section: Introductionmentioning

confidence: 99%

Rh^III‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts

Luo

Gandeepan

Jayakumar

et al. 2013

Chemistry A European J

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An efficient and convenient method for the synthesis of highly substituted polycyclic pyridinium salts from the reaction of various 2-aryl-pyridines and 2-aryl-sp(2) -nitrogen-atom-containing heterocycles with alkynes through rhodium(III)-catalyzed CH activation and annulation under an O2 atmosphere is described. A possible mechanism that involves the chelation-assisted CH activation of the 2-aryl-pyridine substrate, insertion of the alkyne, and reductive elimination is proposed. This mechanism was supported by the isolation of a five-membered rhodacycle (I'). In addition, kinetic isotope studies were performed to understand the intimate reaction mechanism.

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An Efficient Rh/O₂ Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen

Cited by 266 publications

References 76 publications

Increasing Catalyst Efficiency in C−H Activation Catalysis

Increasing Catalyst Efficiency in C−H Activation Catalysis

Advancements in the Synthesis and Applications of Cationic N‐Heterocycles through Transition Metal‐Catalyzed C−H Activation

Rh^III‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts

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An Efficient Rh/O2 Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen

Cited by 266 publications

References 76 publications

Increasing Catalyst Efficiency in C−H Activation Catalysis

Increasing Catalyst Efficiency in C−H Activation Catalysis

Advancements in the Synthesis and Applications of Cationic N‐Heterocycles through Transition Metal‐Catalyzed C−H Activation

RhIII‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts

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An Efficient Rh/O₂ Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen

Rh^III‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts