Nickel-Catalyzed Alkylation of Oxindoles with Secondary Alcohols

Ghosh, Adrija; Banerjee, Debasis

doi:10.1021/acs.joc.3c00402

Cited by 7 publications

(2 citation statements)

References 40 publications

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“…The late-stage functionalisation of cholesterol demonstrated the synthetic potential of the process (Scheme 11). 47…”

Section: Alkylation Reactionmentioning

confidence: 99%

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Bera,

Kabadwal,

Banerjee

2024

Chem. Soc. Rev.

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“…The late-stage functionalisation of cholesterol demonstrated the synthetic potential of the process (Scheme 11). 47…”

Section: Alkylation Reactionmentioning

confidence: 99%

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Bera,

Kabadwal,

Banerjee

2024

Chem. Soc. Rev.

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“…[9] Later, the research group of Morrill and coworkers reported the iron-catalyzed C-alkylation of oxindoles at 150 °C. [10] Contributions from the groups of Gnanaprakasam, [11] Piersanti, [12] Sundararaju, [13] Banerjee, [14] Mitsudome, [15] Beller, [16] Balaraman [17] and Antonino [18] have illustrated that varieties of transition metals (Ru, Ir, Co, Ni, Mn, Ag…) were able to intrigue such alkylation reactions, leading to versatile alkylated oxindoles. Nevertheless, extremely high temperature was needed for these reactions.…”

Section: Introductionmentioning

confidence: 99%

Room‐Temperature Synthesis of α‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction

Song,

Chen,

Huang

et al. 2024

Adv Synth Catal

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Alcohols and oxindoles derivatives are highly important skeletons, widely applicated in both organic and bioorganic chemistry. Herein, we reported a visible‐light‐induced iron‐catalyzed α‐alkylation of oxindoles with alcohols to offer a variety of α‐alkylled oxindoles at room temperature. This reaction featured broad substrate scope with good functional tolerance under simple conditions. Detailed mechanistic studies has been done to illuminate the essetial role of light in this borrowing hydrogen (BH) reaction.

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Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles

Pal,

Guin,

Chakraborty

et al. 2024

ChemCatChem

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Herein we report a sustainable approach for the alkylation of ketones, 9H‐fluorene, oxindole, and indole using alcohols as the alkylating agent catalyzed by a well‐defined air‐stable zinc catalyst (1a) of a tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline (La). 2‐3 mol% of 1a efficiently produces substituted α‐alkylated ketones, 9‐alkylated fluorenes, C3‐alkylated oxindoles, and C3‐alkylated indoles in moderate to good isolated yields. In aerial condition, the formation of bis(indolyl)methane (BIMs) derivatives were observed when indoles were subjected to alkylation by primary alcohols. A few drug molecules containing BIMs were prepared in good isolated yields. The catalyst 1a exhibited good chemoselectivity during the functionalization of fluorene and indole with oleyl alcohol and β‐citronellol. A few control experiments, including deuterium labeling experiments, performed to unveil the reaction mechanism indicate that the one‐electron reduced azo‐anion radical species [1a]‐ formed in situ, acts as the active catalyst. All the redox events occur at the redox‐active aryl‐azo ligand, which acts as the reservoir of hydrogen and electrons throughout the catalytic cycle, keeping the Zn(II)‐center as a template.

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Nickel-Catalyzed Alkylation of Oxindoles with Secondary Alcohols

Cited by 7 publications

References 40 publications

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Room‐Temperature Synthesis of α‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction

Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles

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