Palladium-Catalyzed sp3 C–H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Kanyiva, Kyalo Stephen; Tang, King Hung Nigel; Wang, J.; Shibata, Takanori

doi:10.1055/a-1422-9632

Cited by 6 publications

(2 citation statements)

References 8 publications

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“…Very recently, Kanyiva and Shibata with coauthors successfully modified N-phthaloylalanine derivatives of the type 61 via Pd-catalyzed C(sp 3 )-H benzoxylation using 8-aminoquinolyl group as a DG, tert-butyl hydroperoxide (TBHP) as an oxidant and substituted salicylaldehydes as sources of benzoyl fragments. [56] Under optimized reaction conditions, a broad range of aromatic aldehydes with various substituents was examined, providing the corresponding benzoxylated products 62 with 23-68 % isolated yields (Scheme 10). The unreacted starting materials could be recovered.…”

Section: Acyloxylation Of Aminoacidsmentioning

confidence: 99%

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Antonov

Bryliakov

2022

Applied Organom Chemis

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Herewith, recent progress in the transition metal catalyzed, as well as metal‐free and electrochemical selective acyloxylations of C(sp3)‐H bonds is surveyed. The corresponding modifications of different substrate types such as amines, amides, oximes, aminoacids, nitrogen‐containing heterocycles, olefins, carbonyl compounds, carboxylic acids, and acetals are covered, focusing on their synthetic potential. Correlations between the nature of the catalyst, oxidant, additives, conditions, and the acyloxylation regio‐ and chemoselectivity, are revealed, and available mechanistic details are discussed briefly. The time span of the review is 2015 to present time.

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Section: Acyloxylation Of Aminoacidsmentioning

confidence: 99%

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Antonov

Bryliakov

2022

Applied Organom Chemis

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“…Yu achieved acetoxylation on the methyl carbon of alanine moiety of tripeptides (Scheme 1c) [35]. Recently, Kanyiva and Shibata reported the benzoxylation of alanine derivatives using benzaldehydes as benzoxyl reagents (Scheme 1d) [36]. Since bidentate directing groups were employed in these precedents, substrate scope was limited mostly to sterically less-hindered ones.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids

Matsumura¹,

Usuki²,

Satoh³

2023

Chemistry

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The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid takes place via ring-opening to selectively afford an acyclic γ-acetoxy-α,β-unsaturated amino acid.

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Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

et al. 2022

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C(sp 3 )À H functionalization is a core part of organic chemistry because of the presence of C(sp 3 )À H bonds in various organic molecules. However, since most C(sp 3 )À H bonds are non-reactive, their functionalization is an uphill task. Standard methods of functionalization employ prefunctionalized reactants, expensive organometallic reagents, strong acids or bases and similar other harsh reaction conditions. These methods eventually affect the reaction and prevent it from yielding optimum results. Transition metalbased catalysts like Pd, Rh and Ru provide a direct functionalization route without unwanted pre-functionalization steps. These catalysts furnish superior results under mild reaction conditions. But, their expense, toxicity and low natural abundance prevent them from achieving ideality. Therefore, 3d transition metal catalysts like Mn, Fe, Co, Ni and Cu catalysts have gained significance as an alternative for conventional transition metal catalysts due to their high natural abundance, low toxicity and affordability. Copperbased catalysts are particularly important owing to the wide range of oxidation states of copper and the facile tunability of their catalytic properties. Hence, an immense amount of research is being conducted on the catalytic activity of copper for C(sp 3 )À H functionalization. This review aims to provide a detailed overview of some recent reports on C(sp 3 )À H functionalization using catalytic systems based on copper.

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Palladium-Catalyzed sp3 C–H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Cited by 6 publications

References 8 publications

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

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Palladium-Catalyzed sp3 C–H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Cited by 6 publications

References 8 publications

Recent progress in catalytic acyloxylation of C(sp3)‐H bonds

Recent progress in catalytic acyloxylation of C(sp3)‐H bonds

Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp3)−H Bonds

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Product

Resources

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Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds