Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes

Wang, Shaohua; Liu, Wenjie; Cen, Jinghe; Liao, Jinqiang; Huang, Jianping; Zhan, Hui

doi:10.1016/j.tetlet.2014.01.069

Cited by 55 publications

(24 citation statements)

References 44 publications

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“…3‐[4‐( tert ‐Butyl)phenyl]‐2‐phenylimidazo[1,2‐ a ]pyridine (3w): [9e] Column chromatography on silica gel (20 % EtOAc/hexane) afforded 3w (55.4 mg, 68 % yield) as a solid. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.96 (d, J = 6.8 Hz, 1 H), 7.67 (t, J = 7.8 Hz, 3 H), 7.52 (d, J = 7.8 Hz, 2 H), 7.36 (d, J = 7.7 Hz, 2 H), 7.28 (t, J = 7.5 Hz, 2 H), 7.23 (dd, J = 12.6, 5.9 Hz, 1 H), 7.19–7.15 (m, 1 H), 6.70 (t, J = 6.6 Hz, 1 H), 1.39 (s, 9 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

“…In particular, 3‐aryl‐substituted imidazo[1,2‐ a ]pyridines have diverse biological activities . As a result, a variety of synthetic methods have been developed for their preparation that use various transition‐metal catalysts and aryl sources such as haloarenes and phenylboronic acids . The development of metal‐free conditions for the arylation of imidazo[1,2‐ a ]pyridines is desirable because of the resulting milder reaction conditions, less expensive reagents, and lack of residual metallic impurities in the final products.…”

Section: Introductionmentioning

confidence: 99%

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Base‐Promoted Transition‐Metal‐Free Arylation of Imidazo‐Fused Heterocycles with Diaryliodonium Salts

et al. 2018

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Potassium tert‐butoxide was used to promote the arylation of imidazo‐fused heterocycles with diaryliodonium salts under transition‐metal‐free conditions. The described process proceeds through a radical pathway without the addition of oxidants or additives. A number of functional groups were tolerated in this transformation, which provided good to excellent yields of the arylation products.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Base‐Promoted Transition‐Metal‐Free Arylation of Imidazo‐Fused Heterocycles with Diaryliodonium Salts

et al. 2018

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“…5 [27] PhSi(OMe)3, Pd(OAc)2, AgF, dioxane, 80 °C, 16h [32] Benzene, Pd(OAc)2, O2, HOAc, DMA, 130 °C, 20h…”

Section: Literature Validationmentioning

confidence: 99%

In Silico Rationalisation of Selectivity and Reactivity in Pd-Catalysed C-H Activation Reactions

Cao¹,

Kabeshov²,

Ley³

et al. 2020

Preprint

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<p>A computational approach has been developed to automatically generate and analyse the structures of the intermediates of palladium catalysed carbon-hydrogen (C-H) activation reactions as well as to predict the final products. Implemented as a high-performance computing cluster tool, it has been shown to correctly choose the mechanism and rationalise regioselectivity of chosen examples from open literature reports. The developed methodology is capable of predicting reactivity of various substrates by differentiation between two major mechanisms - proton abstraction and the electrophilic aromatic substitution. An attempt has been made to predict new C-H activation reactions. This methodology can also be used for the automated reaction planning, as well as a starting point for microkinetic modelling.</p>

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“…The reaction was supposed to proceed via C–H cleavage at the 3-position of 375 followed by coordination from 77 and reductive elimination to yield the final product (Scheme 148). The group of Wang and Liu [203] has developed a more facile and versatile approach than that of Cao et al [204] for the regioselective arylation of 375 . The noteworthy aspect of their methodology was Pd(OAc) 2 -catalyzed cross coupling with unactivated arenes 451 .…”

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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Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes

Cited by 55 publications

References 44 publications

Base‐Promoted Transition‐Metal‐Free Arylation of Imidazo‐Fused Heterocycles with Diaryliodonium Salts

Base‐Promoted Transition‐Metal‐Free Arylation of Imidazo‐Fused Heterocycles with Diaryliodonium Salts

In Silico Rationalisation of Selectivity and Reactivity in Pd-Catalysed C-H Activation Reactions

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

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