Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

Sheng, Xing; Xian, Jiayi; Liu, Shuting; Zhang, Xiangyu; Li, Bin; Wang, Jun; Chen, Xiuwen; Xie, Feng

doi:10.1016/j.jcat.2023.03.019

Cited by 7 publications

(3 citation statements)

References 37 publications

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“…In 2022, while studying the selective hydrogenation coupling of nitroaromatics and phenol under palladium catalysis, Xie's group [11] discovered by chance that N-(2nitrophenyl)pyrrole could react with nitrile to give pyrrolo[1,2α]quinoxalines. In 2023, Xie's group [12] successfully synthesized pyrrolo[1,2-α]quinoxalines using nitrile based on palladiumcatalysed transfer hydrogenation strategy.…”

Section: Palladium Catalysis Systemmentioning

confidence: 99%

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Liu

Wang

2023

Asian J Org Chem

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Pyrrolo[1,2‐α]quinoxaline and its derivatives have excellent biological activity and photoelectric properties, and are widely used in the fields of pharmaceutical preparations and organic electroluminescence. This review starts from catalysts and summarizes the single metal catalysis of palladium, rhodium, iron, molybdenum, and copper, as well as the synergistic catalysis of iron molybdenum bimetallic and metal‐free catalytic systems for the synthesis of pyrrolo[1,2‐α]quinoxaline. The pyrrolo[1,2‐α]quinoxaline catalytic mechanism in the different catalytic systems was detailly introduced and analysed. By analysing the advantages and disadvantages of existing catalyst systems, the prospects of new catalysts and methods for synthesis of pyrrolo[1,2‐α]quinoxaline are presented.

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Section: Palladium Catalysis Systemmentioning

confidence: 99%

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Liu

Wang

2023

Asian J Org Chem

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“…As a continuation of our contributions toward the construction or functionalization of nitrogen heterocycles using heterogeneous catalysts, [13] we recently reported a POP-supported nano-ruthenium-catalyzed cascade aromatization of quinoxalin-2(1H)-one with alkynes to produce furo [2,3-b]quinoxaline compounds. [14] In particular, these POP materials exhibited excellent regioselectivity and recyclability for CÀ H functionalization.…”

mentioning

confidence: 99%

“…A temperature screening (entry 11) showed that 100 °C was sufficient for the reaction. Finally, we compared the catalytic performance of POPÀ NADÀ Ir in the model reaction with other relevant materials, including the catalyst precursor (entry 12), various homogeneous precious metals (entries [13][14][15], and related nanocatalysts (entries 16-19). The results showed that POPÀ NADÀ Ir exhibited the best activity.…”

mentioning

confidence: 99%

Recyclable Iridium Catalyst Supported on Porous Organic Polymer for Acceptorless Dehydrogenative Silylation: Synthesis of Ring‐Fused Oxasilacycles

Xian,

Sheng,

Lin

et al. 2024

Adv Synth Catal

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The direct conversion of specific C–H bonds to C–Si bonds in alkanes or aromatics via catalytic methods has attracted growing research interest. Herein, we report the preparation of a new iridium catalyst supported on a naphthyridine‐based porous organic polymer and its successful application in the dehydrogenative silylation of 2‐arylphenols or alcohol and hydrosilanes to access ring‐fused oxasilacycles. The synthetic method exhibits broad substrate scope and good functional group compatibility while avoiding the use of hydrogen acceptors. In addition, this organic polymer supported iridium catalyst could be easily recovered from the reaction system and reused for at least seven times without apparent deactivation. This research provides new insights for the further design of heterogeneous nanocatalysts and contributes to the synthesis of silicon‐substituted functional molecules.

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Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Sun,

Miao,

et al. 2024

Adv Synth Catal

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A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐a]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH3CN has been developed, which includes the functionalization of C(sp3)‐H bonds as well as the construction of C‐C and C‐N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH3CN in this reaction acts as both a carbon source via C‐C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐a]quinoxaline derivatives were obtained.

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Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

Cited by 7 publications

References 37 publications

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Recyclable Iridium Catalyst Supported on Porous Organic Polymer for Acceptorless Dehydrogenative Silylation: Synthesis of Ring‐Fused Oxasilacycles

Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

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Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

Cited by 7 publications

References 37 publications

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Recyclable Iridium Catalyst Supported on Porous Organic Polymer for Acceptorless Dehydrogenative Silylation: Synthesis of Ring‐Fused Oxasilacycles

Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

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Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation