N-Heterocyclic carbene–palladium(<scp>ii</scp>)–1-methylimidazole complex catalyzed direct C–H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides

Liu, Qing-Xian; He, Bangyue; Qian, Peng‐Cheng; Shao, Li‐Xiong

doi:10.1039/c6ob02704k

Cited by 19 publications

(9 citation statements)

References 44 publications

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“…The residue was purified by column chromatography on silica gel (EtOAc/ hexane) to give the desired products 2-6, 8-12 and 14. -imidazo[1,2-a]pyridine2 30a, 35,36 . The generale procedure afforded 138 mg (84% yield) of the title compound.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectrum matched that of the literature. [1,2,a]pyridine 3 35,36 . The generale afforded 138 mg (78% yield) of the title compound.…”

Section: Methodsmentioning

confidence: 99%

“…With these reaction conditions in hand, we evaluated then the scope and limitations of our method using various imidazo[1,2-a] pyridine analogues (Table 1). When 4-bromotoluene, 3-bromotulene or 2-bromotoluene were used as coupling partners, the desired products 3-5 were obtained in 78 35 , 81 30a and 75% 35 yields, respectively (entries 2-4, Table 1). This result shows no real impact of the position of the methyl group on the reaction yield.…”

Section: Scheme 1 Optimization Of C-h Arylation Of Imidazo[12-a] Pymentioning

confidence: 99%

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Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation

Abbouchi

Koubachi

Brahmi³

et al. 2019

Mediterr.J.Chem.,

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A short and practical arylation of imidazo[1,2-a]pyridine and imidazole derivatives with aryl halides or aryl boronic acids as coupling partners was successfully carried out using phosphine-free (SIPr)Pd(allyl)Cl as the catalyst [SIPr: (N,N’-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)] ((SIPr)Pd(allyl)Cl complex). 3,6-disubstituted imidazo[1,2-a]pyridine and 5-substituted imidazole compounds were obtained in good to excellent yields in only 1h under microwave-assisted C-H arylation and Suzuki-Miyaura coupling reaction conditions.

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Section: Methodsmentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectrum matched that of the literature. [1,2,a]pyridine 3 35,36 . The generale afforded 138 mg (78% yield) of the title compound.…”

Section: Methodsmentioning

confidence: 99%

Section: Scheme 1 Optimization Of C-h Arylation Of Imidazo[12-a] Pymentioning

confidence: 99%

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Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation

Abbouchi

Koubachi

Brahmi³

et al. 2019

Mediterr.J.Chem.,

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“…Decarboxylation of this intermediate followed by reductive elimination led to the formation of the 3-arylated product along with the reduction of Pd(II) to Pd(0) (Scheme 159). The group of Liu and He have reported a direct C–H bond arylation reaction of 375 with aryl chloride 466 [209]. The group has developed an N-heterocyclic carbine–Pd(II) [NHC-Pd(II)] complex which was found to be effective towards C–C, C–N coupling and C–H arylation reactions (Scheme 160).…”

Section: Reviewmentioning

confidence: 99%

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Reen

Kumar

Sharma

2019

Beilstein J. Org. Chem.

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A comprehensive account of recent advances in the synthesis of imidazopyridines, assisted through transition-metal-catalyzed multicomponent reactions, C–H activation/functionalization and coupling reactions are highlighted in this review article. The basic illustration of this review comprises of schemes with concise account of explanatory text. The schemes depict the reaction conditions along with a quick look into the mechanism involved to render a deep understanding of the catalytic role. At some instances optimizations of certain features have been illustrated through tables, i.e., selectivity of catalyst, loading of the catalyst and percentage yield with different substrates. Each of the reported examples has been rigorously analyzed for reacting substrates, reaction conditions and transition metals used as the catalyst. This review will be helpful to the chemists in understanding the challenges associated with the reported methods as well as the future possibilities, both in the choice of substrates and catalysts. This review would be quite appealing to a wider range of organic chemists in academia and industrial R&D sectors working in the field of heterocyclic syntheses. In a nutshell, this review will be a guiding torch to envisage: (i) the role of various transition metals in the domain dedicated towards method development and (ii) for the modifications needed thereof in the R&D sector.

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“…The synthesized complexes have been highly active catalysts in our study when compared to the similar studies related to bis(NHC)Pd(II) complexes published. 43,[55][56][57][58][59][60][61][62]…”

Section: Direct Arylation Of 2-n-butylfuran and 2-nbutylthiophene Witmentioning

confidence: 99%

Novel 2-hydroxyethyl substituted N-coordinate-Pd(II)(NHC) and bis(NHC)Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction

2019

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The direct arylation reaction has attracted attention in recent years especially because of its environment-friendly properties. In this study, we researched the synthesis of 2-hydroxyethyl substituted bis(NHC)Pd(II) complexes and also the synthesis of N-coordinate-Pd(II)(NHC) complexes containing Nbound benzimidazolium from palladium acetate ([Pd(CH 3 COO) 2 ]) with 1,3-disubstituted benzimidazolium halides in DMSO. All the complexes have been characterized by using 1 H NMR, 13 C NMR, FTIR spectroscopy and elemental analysis techniques. The molecular and crystal structure of one of the complexes is confirmed by using single-crystal X-ray diffraction. These complexes have been examined as the catalyst in the direct arylation reaction with 2-n-butylfuran and 2-n-butylthiophene and have demonstrated excellent activity in this reaction.

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N-Heterocyclic carbene–palladium(ii)–1-methylimidazole complex catalyzed direct C–H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides

Cited by 19 publications

References 44 publications

Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation

Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Novel 2-hydroxyethyl substituted N-coordinate-Pd(II)(NHC) and bis(NHC)Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction

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