Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4<i>H</i>‐Benzo[<i>d</i>][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

Gupta, Mohit; Bahadur, Vijay; Parmar, Virinder S.; Kumar, Prashant

doi:10.1002/ejoc.201800263

Cited by 24 publications

(4 citation statements)

References 95 publications

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“…The structures of the compounds 3a and 3f were also confirmed by the single-crystal X-ray analysis (Figure 1). [22] Figure 1. Single crystal X-ray structures of compounds 3a and 3f.…”

Section: Resultsmentioning

confidence: 99%

Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

et al. 2018

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Toluenes, aldehydes, and benzyl alcohols have been utilized in the radical‐induced direct functionalization of 4H‐benzo[d][1,3]oxazin‐4‐one derivatives by using a palladium‐catalyzed C–H activation strategy. The stability, low toxicity, and ease of access to toluenes, aldehydes, and benzyl alcohols have made them suitable candidates for this transformation. The reaction proceeded smoothly with high functional group compatibility and afforded the desired products in moderate to good yields. Mechanistic investigations illustrate the radical pathway and highlight the importance of both catalyst and oxidant.

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“…The structures of the compounds 3a and 3f were also confirmed by the single-crystal X-ray analysis (Figure 1). [22] Figure 1. Single crystal X-ray structures of compounds 3a and 3f.…”

Section: Resultsmentioning

confidence: 99%

Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

et al. 2018

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“…reported a highly effective palladium‐catalyzed C–N/C–C bond formation approach to access 6a‐phenyl‐5 H ‐benzo[4,5][1,3]oxazino[2,3‐ a ]isoindole‐5,11‐(6a H )‐diones 263 from 4 H ‐benzo[ d ][1,3]oxazin‐4‐one derivatives 261 , toluenes, aldehydes, and benzyl alcohols 262 (Scheme 73). [55] All toluene derivatives showed good compatibility to this reaction. Additionally, a series of benzaldehyde derivatives bearing electron‐donating or electron‐withdrawing groups were tested and excellent yields were obtained.…”

Section: Pd(iii) Involved Reactionsmentioning

confidence: 90%

Recent Progress in Palladium‐Catalyzed Radical Reactions

Sun

Liu

et al. 2021

Adv Synth Catal

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In recent years, great improvements have been made on palladium‐catalyzed radical reactions. Emerging elegant methodologies of radical involved palladium‐catalyzed transformations provide more and more effective strategies for the construction of complex heterocyclic compounds and applications in drug discovery. It is universally known that Pd(0)/(II)/(IV)‐mediated reactions usually undergo two‐electron transfer processes, while the Pd(I) and Pd(III) involved reactions usually occur via single electron transfer processes. Since our review on palladium radical was published, numurous methodolgies involving palladium radical have sprung up in the past five years. This review further summarized the up‐to‐date transformations toward palladium radical from 2015. For most of these catalytic cycles strategies, plausible mechanisms are demonstrated in detail to give better insight for chemists in need.

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“…This methodology wasf urther implemented to functionalization of 4H-Benzo[d][1,3]oxazin-4-onest of used tetracyclic compounds containing the isoindolinone moiety by Kumare tal. [30] (Scheme 5C).…”

Section: Pd-catalyzed Cyclization Using Acyl Radicalsmentioning

confidence: 99%

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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Isoindolinone structure is an important privileged scaffold found in al argev ariety of naturallyo ccurring as well as synthetic, biologically and pharmaceutically active compounds. Owing to its crucial role in anumber of applications, the synthetic methodologies for accessingt his heterocyclic skeleton have received significant attentiond uring the past decade. In general, the synthetic strategies can be divided into two categories:F irst, direct utilization of phthalimides or phthalimidines as startingm aterials for the synthesis of isoindolinones;a nd second, construction of the lactam and/or aromatic rings by different catalytic methods, including CÀHa ctivation, cross-coupling,c arbonylation, condensation, addition and formal cycloaddition reactions. Especially in the last mentioned, utilization of transition metal catalysts provides access to ab road range of substituted isoindolinones.H erein, the recent advances (2010-2020) in transition metal catalyzed synthetic methodologies via formation of new CÀCbonds for isoindolinones are reviewed.

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Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

Cited by 24 publications

References 95 publications

Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

Radical‐Induced, Palladium‐Catalyzed C–H Activation: An Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

Recent Progress in Palladium‐Catalyzed Radical Reactions

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

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