Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: a facile synthesis of 2-arylpyrroles

Du, Wei; Zhao, Mi‐Na; Z, Ren; Wang, Yao‐Yu; Zhang, Guan

doi:10.1039/c4cc03129f

Cited by 79 publications

(17 citation statements)

References 57 publications

(2 reference statements)

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“…In 2014, Guan et al. developed a facile protocol to synthesize 2‐arylpyrroles via intramolecular 5‐ endo ‐trig cyclization of ketoxime carboxylates catalyzed by copper (Scheme ) . A series of β,γ‐unsaturated aryl ketoxime esters was investigated, leading to substituted 2‐arylpyrroles in good yields (Scheme ).…”

Section: Heck‐type Reactionsmentioning

confidence: 99%

Transition Metal‐Catalyzed Reactions Involving Oximes

Zhang

et al. 2017

Adv Synth Catal

117

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Oximes are an easily prepared and transformed unit, which are widely used in organic synthesis. The oximes, including oxime ethers and esters, could realize various transformations, such as C–H bond activation, Heck‐type reactions, N–O bond cleavage/C–N bond formation, O–H bond cleavage and couplings. However, there is no a comprehensive review on this subject. Herein, we summarize the recent advances over the past 15 years in transition metal‐catalyzed reactions involving oximes, focusing on the reaction scope, limitations and mechanisms.

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Section: Heck‐type Reactionsmentioning

confidence: 99%

Transition Metal‐Catalyzed Reactions Involving Oximes

Zhang

et al. 2017

Adv Synth Catal

117

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“…Copper‐catalyzed cyclization of γ,δ‐unsaturated O ‐acyl oximes [9a] and β,γ‐unsaturated O ‐acyl oximes [23] to dihydropyrroles and pyrroles via iminyl radical intermediates is known. However, these competitive reactions were not observed under our present reaction conditions in the preparation of compounds 1 m , 1 y and 1 aa .…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

et al. 2021

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Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.Scheme 1. Ynimines: structure and synthesis.

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“…In 2014, Guan's group reported a novel and efficient Cu(I)‐catalyzed intramolecular 5‐ exo ‐trig cyclization of ketoxime carboxylates for rapid synthesis of a wide range of 2‐arylpyrroles under mild conditions (Scheme 12). [18] Notably, alkylpyrrole could also be synthesized in 51% yield by this method. In addition, different carboxylates of 1‐phenylbut‐3‐en‐1‐one oxime such as propionate, pivalate, and benzoate can also tolerate with this transformation to give target products in good yields.…”

Section: Radical Strategies For Cyclization Of βγ‐Unsaturated Hydrazones and Oximesmentioning

confidence: 99%

Radical Cascade Reactions of β,γ‐Unsaturated Hydrazones/Oximes

2021

Adv Synth Catal

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Radical cascade cyclization of β,γ‐unsaturated hydrazones/oximes has recently emerged as an efficient and powerful protocol for the construction of diverse and valuable functionalized pyrazolines and isoxazolines. In this review, three catalytic ways of radical cascade cyclization of β,γ‐unsaturated hydrazones/oximes are summarized and classified; these are transition‐metal‐catalyzed systems, transition‐metal‐free systems, and photo‐/electrocatalytic systems, respectively. Through these methods, various functional groups are installed on the pyrazoline and isoxazoline skeletons to enrich the small organic molecule library.

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Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: a facile synthesis of 2-arylpyrroles

Cited by 79 publications

References 57 publications

Transition Metal‐Catalyzed Reactions Involving Oximes

Transition Metal‐Catalyzed Reactions Involving Oximes

Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

Radical Cascade Reactions of β,γ‐Unsaturated Hydrazones/Oximes

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