Ppm Cu Catalyst Enables <i>tert</i>-Alkylation Followed by C–H Cyclization To Synthesize Substituted Oxindoles

Yoshinaga, Kohei; Tsubaki, Naoya; Murata, Yumi; Noda, Yujiro; Nishikata, Takashi

doi:10.1021/acsomega.8b01397

Cited by 8 publications

(1 citation statement)

References 71 publications

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“…The catalytic reaction proceeds by a tandem process involvin tert ‐alkylation followed by subsequent C−H cyclization to form the corresponding substituted oxindoles in good to excellent yields and high TON (See Figure 88). [124] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis.

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Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Nishikata

2024

ChemistryOpen

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This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. This α‐bromocarbonyl compound with a tertiary carbon has been used primarily only as a radical initiator in atom transfer radical polymerization (ATRP) reactions. However, with the recent development of photo‐radical reactions (around 2010), research on the use of α‐bromocarbonyl compounds as tertiary alkyl radical precursors became popular (around 2012). As more examples were reported, α‐bromocarbonyl compounds were studied not only as radicals but also for their applications in organometallic and ionic reactions. That is, α‐bromocarbonyl compounds act as nucleophiles as well as electrophiles. The carbonyl group of α‐bromocarbonyl compounds is also attractive because it allows the skeleton to be converted after the reaction, and it is being applied to total synthesis. In our survey until 2022, α‐bromocarbonyl compounds can be used to perform a full range of reactions necessary for organic synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific reactions, asymmetric reactions. α‐Bromocarbonyl compounds have created a new trend in tertiary alkylation, which until then had limited reaction patterns in organic synthesis. This review focuses on how α‐bromocarbonyl compounds can be used in synthetic organic chemistry.

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Copper catalysis for saturated N-heterocycles via C–H functionalization

Gandeepan

2021

Copper in N-Heterocyclic Chemistry

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Ppm Cu Catalyst Enables tert-Alkylation Followed by C–H Cyclization To Synthesize Substituted Oxindoles

Cited by 8 publications

References 71 publications

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Copper catalysis for saturated N-heterocycles via C–H functionalization

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