Pd and photoredox dual catalysis assisted decarboxylative <i>ortho</i>-benzoylation of <i>N</i>-phenyl-7-azaindoles

Rajput, Shruti; Kaur, Ramandeep; Jain, Nidhi

doi:10.1039/d1ob02338a

Cited by 11 publications

(7 citation statements)

References 83 publications

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“…Recently, Jain's group [20] disclosed a protocol for the synthesis of benzoylated N-aryl-7-azaindoles under the assistance of Pd and photoredox dual catalysis (Scheme 10). They used α-keto acids as benzoyl radical precursors to realize the benzoylation of N-phenyl-7-azaindoles through radical decarboxylative coupling.…”

Section: C-h Benzoylation Of N-aryl-7-azaindolesmentioning

confidence: 99%

Recent Advances in the N-Aryl C—H Functionalization Using 7-Azaindole as Intrinsic Directing Group

Yuan¹,

Pan²

2023

Chinese Journal of Organic Chemistry

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The intrinsic directing group is a functional group in the substrates and also serves as an essential component in products. Thus, the preinstallation and removal of directing groups are avoided. 7-Azaindole has been used as intrinsic directing group for the N-aryl-C-H functionalization of N-aryls under the catalysis of transition metals. Utilizing the C-H functionalization strategy, numerous functional groups were installed into the ortho-position of N-aryls of the corresponding N-aryl-7-azaindoles. In this review, the recent achievements on the transition-metal catalyzed N-aryl ortho-C-H functionalization directed by 7-azaindole are summarized.

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Section: C-h Benzoylation Of N-aryl-7-azaindolesmentioning

confidence: 99%

Recent Advances in the N-Aryl C—H Functionalization Using 7-Azaindole as Intrinsic Directing Group

Yuan¹,

Pan²

2023

Chinese Journal of Organic Chemistry

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“…Recently, Jain et al described ortho-benzoylation of N-aryl-7-azaindoles with α-keto acids through the merger of visible light photoredox catalysis and Pd catalysis. [23] They employed Eosin Y as photocatalyst and silver nitrate as additive under O 2 environment. The use of silver salt facilitates benzoyl radical formation which in turn increases the yield of the desired benzoylated product.…”

Section: Cà H Acylationmentioning

confidence: 99%

“…Recently, Jain et al. described ortho‐benzoylation of N‐aryl‐7‐azaindoles with α‐keto acids through the merger of visible light photoredox catalysis and Pd catalysis [23] . They employed Eosin Y as photocatalyst and silver nitrate as additive under O 2 environment.…”

Section: C−h Functionalizationmentioning

confidence: 99%

Dual Palladium‐Photoredox Catalyzed C−H functionalization

Saha

Gopinath

2022

Eur J Org Chem

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Functionalization of unactivated CÀ H bonds is a highly desirable process in organic chemistry as it gives direct access to new functional groups in a single step. This process is generally achieved using transition metal catalysts, and among them, palladium plays an important role due to its unique reactivity. Recently, photoredox catalysis has witnessed a huge surge, and many new and valuable organic reactions are uncovered periodically. Dual transition metal -photoredox catalysis on the other hand, has taken organic synthesis to new heights by achieving transformations that were previously not possible or difficult to achieve by both forms of catalysis independently. In this direction, many new and interesting dual palladium-photoredox catalyzed CÀ H functionalization reactions combining the synergistic effects of both palladium and photoredox have been reported in the past few years, and it is imperative to summarize these reactions for further developments in this area.

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“…Copper(I)-promoted hydroxytrifluoromethylation of enamides to substituted 3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-ones was reported by Zeng and co-workers (Scheme C-vi) in 2018 . Continuing our ongoing research in visible light-mediated chemical transformations under mild conditions, we explored the feasibility of photocatalyzed synthesis of 3-benzyl-3-hydroxyisoindolin-1-ones in visible light. We anticipated that a Meerwein-photocatalytic approach might work on N -substituted 3-methyleneisoindolin-1-ones as starting materials and enable difunctionalization at the double bond.…”

Section: Introductionmentioning

confidence: 99%

Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light

Kumar

Jain

2022

J. Org. Chem.

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Mild and efficient ruthenium-catalyzed hydroxy-arylation of the terminal double bond of N-substituted 3-methyleneisoindolin-1-ones is described. The reaction takes place with aryl diazonium salt as the arylating reagent and water as the hydroxyl source in visible light at ambient temperature. The strategy entails vicinal difunctionalization of alkene and enables construction of 3-benzyl-3-hydroxyisoindolin-1-one heterocyclic scaffolds in moderate to good yields. C–C and C–O bonds are formed in one pot without any external additive and oxidant through an in situ generation of a carbocation intermediate in green light.

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Pd and photoredox dual catalysis assisted decarboxylative ortho-benzoylation of N-phenyl-7-azaindoles

Abstract: Directing group assisted decarboxylative ortho-benzoylation of N-aryl-7-azaindoles with α-keto acids has been achieved by synergistic visible light promoted photoredox and palladium catalysis. The approach tenders rapid entry to aryl ketone...

Cited by 11 publications

References 83 publications

Recent Advances in the N-Aryl C—H Functionalization Using 7-Azaindole as Intrinsic Directing Group

Recent Advances in the N-Aryl C—H Functionalization Using 7-Azaindole as Intrinsic Directing Group

Dual Palladium‐Photoredox Catalyzed C−H functionalization

Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light

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