Iodine-Catalyzed One-Pot Synthesis of<i>α</i>-Ketoamides from Unsaturated Hydrocarbons

任相伟,; 王光伟,; 唐向阳,; 赵温涛,

doi:10.6023/cjoc201502014

Cited by 4 publications

(1 citation statement)

References 6 publications

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“…Intriguingly, just a few months after Shah’s report, Ren et al obtained very similar results in their I 2 /TBHP/DMSO-mediated oxidative amidation of unsaturated hydrocarbons.…”

Section: Amidation Approachesmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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The α-ketoamide motif is widely found in many natural products and drug candidates with relevant biological activities. Furthermore, α-ketoamides are attractive candidates to synthetic chemists due to the ability of the motif to access a wide range of functional group transformations, including multiple bond-forming processes. For these reasons, a vast array of synthetic procedures for the preparation of α-ketoamides have been developed over the past decades, and the search for expeditious and efficient protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged since the 1990s up to the present. The different synthetic routes have been grouped according to the way the α-ketoamide moiety has been created. Thus, syntheses of α-ketoamides proceeding via C(2)-oxidation of amide starting compounds are detailed, as are amidation approaches installing the α-ketoamide residue through C(1)-N bond formation. Also discussed are the methodologies centered on C(1)-C(2) σ-bond construction and C(2)-R/Ar bond-forming processes. Finally, the literature regarding the synthesis of α-ketoamide compounds by palladium-catalyzed double-carbonylative amination reactions is discussed.

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“…Intriguingly, just a few months after Shah’s report, Ren et al obtained very similar results in their I 2 /TBHP/DMSO-mediated oxidative amidation of unsaturated hydrocarbons.…”

Section: Amidation Approachesmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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One‐Pot Synthesis of p‐Amino‐Substituted Unsymmetrical Benzils and Benzil Derivatives

et al. 2017

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An efficient iodine/copper(II) oxide co‐promoted direct oxidative coupling of anilines and methyl aryl ketones has been developed for the synthesis of p‐amino‐substituted unsymmetrical benzils and their iodo‐substituted derivatives. The chemoselectivity of the reactions can be easily controlled by adjusting the amount of iodine. This method exhibits good functional group tolerance for various substituents on the aromatic rings of the methyl aryl ketones. A possible mechanism for this reaction has been proposed based on control experiments. A couple of representative quinoxalines were synthesized from the benzil products in order to demonstrate the utility of this approach.magnified image

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A photosensitized metal free approach to α‐ketoamides:sequential oxidative amidationdiketonization of terminal alkynes

et al. 2021

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A novel transition metal‐free photosensitized protocol has been developed for the synthesis of α‐ketoamides via oxidative coupling of alkynes and amines in the presence of thiophenol under visible light irradiation and rose bengal dye. A series of alkynes with both electron‐donating and electron‐withdrawing groups were successfully employed for the synthesis of their corresponding α‐ketoamides. This reaction presents a benign visible light based milder synthetic methodology with broad functional‐group tolerance.

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Iodine-Catalyzed One-Pot Synthesis ofα-Ketoamides from Unsaturated Hydrocarbons

Cited by 4 publications

References 6 publications

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

One‐Pot Synthesis of p‐Amino‐Substituted Unsymmetrical Benzils and Benzil Derivatives

A photosensitized metal free approach to α‐ketoamides:sequential oxidative amidationdiketonization of terminal alkynes

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