Silver-catalyzed radical cascade cyclization of 1,3-diarylpropynones with 1,3-dicarbonyl compounds to access 2-dicarbonyl indenones

Li, Zhenhua; Ma, Yao; Qin, Jinjing; Tan, Zhiqiang; Sun, Xiu‐Li; Wang, Wenbiao

doi:10.1016/j.tetlet.2020.151679

Cited by 6 publications

(2 citation statements)

References 49 publications

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“…[14] Recently, Li's group developed a silvercatalyzed radical cascade cyclization of ynones with the α-C(sp 3 )À H bond in 1,3-dicarbonyl compounds. [15] However, the silver catalyst and 1,3-dicarbonyl skeletons were necessary in this transformation. To our knowledge, the alkylation of ynones with the α-C(sp 3 )À H bond in acetone for the synthesis of alkylation indenone derivatives has not been established under transition-metal-free conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Acetone is a common starting material for the building of new carbon‐carbon bonds via the direct activation of α ‐C(sp 3 )−H bonds [13] and the products are really important skeletons in pharmaceutical molecules [14] . Recently, Li's group developed a silver‐catalyzed radical cascade cyclization of ynones with the α ‐C(sp 3 )−H bond in 1,3‐dicarbonyl compounds [15] . However, the silver catalyst and 1,3‐dicarbonyl skeletons were necessary in this transformation.…”

Section: Introductionmentioning

confidence: 99%

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K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

Tian,

Xiong,

Xiong

et al. 2023

ChemistrySelect

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A simple and efficient oxidative‐promoted radical cascade annulation of ynone derivatives with ketones for the construction of a series of oxoalkyl‐substituted indenones in moderate to good yields is described. The control experiment results indicate that the oxidative acetmethylation/arylation of ynone derivatives involves a radical cascade cyclization process. This is an operationally simple and efficient protocol which will be attractive in organic synthesis chemistry.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

Tian,

Xiong,

Xiong

et al. 2023

ChemistrySelect

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Highly Selective Monoalkylation of Active Methylene and Related Derivatives using Alkylsilyl Peroxides by a Catalytic CuI‐DMAP System

Zhou

Wang

et al. 2021

Asian J Org Chem

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A new approach for highly selective monoalkylation of active methylene and related derivatives using various types of alkylsilyl peroxides in the presence of copper catalysts under mild conditions has been developed to a synthetically useful level. This approach has a wide substrate scope in terms of both active methylene compounds and alkylsilyl peroxides. In addition, nitroalkanes can also be employed for a copper‐catalyzed selective monoalkylation with alkylsilyl peroxides. The participation of radical species was proposed in the present monoalkylation reactions by the mechanistic study.

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Solvothermal Fabrication of NiO/Co₃O₄ Spherical Composites Modified with N‐Doped Graphene Quantum Dots as a Catalyst in the Microwave‐Assisted Synthesis of Spiro[diindenopyridine‐indoline] Triones

2021

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N‐Doped Graphene Quantum Dots (N‐GQDs) have been extensively investigated owing to their interesting photochemical, and electrochemical properties. However, N‐GQDs have rarely been introduced as catalyst in organic reactions. Herein, NiO/Co3O4 composites with diverse morphologies of hexagonal nanoplates, spherical, irregular nanocubics, and multishape are fabricated using different solvents and pH adjusters. In the following, the catalytic activity of engineered composites was screened, and it demonstrated to be in the order: spherical>hexagonal nanoplate>irregular solid nanocubic>multi‐shape. The uniform spherical morphology makes exposure of a larger part of the reactive facets possible and provides accessible active sites. Next, novel NiO/Co3O4@N‐GQDs spherical composites has been successfully fabricated by cost‐effective, green and straightforward hydrothermal method. Proposed composite was applied as an efficient heterogeneous catalyst for the microwave‐assisted synthesis of new and known indenospiro derivatives. The desired products were formed in excellent yields (88–97 %) within the short reaction time (6–14 min).

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Silver-catalyzed radical cascade cyclization of 1,3-diarylpropynones with 1,3-dicarbonyl compounds to access 2-dicarbonyl indenones

Cited by 6 publications

References 49 publications

K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

Highly Selective Monoalkylation of Active Methylene and Related Derivatives using Alkylsilyl Peroxides by a Catalytic CuI‐DMAP System

Solvothermal Fabrication of NiO/Co₃O₄ Spherical Composites Modified with N‐Doped Graphene Quantum Dots as a Catalyst in the Microwave‐Assisted Synthesis of Spiro[diindenopyridine‐indoline] Triones

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Silver-catalyzed radical cascade cyclization of 1,3-diarylpropynones with 1,3-dicarbonyl compounds to access 2-dicarbonyl indenones

Cited by 6 publications

References 49 publications

K2S2O8‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

K2S2O8‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

Highly Selective Monoalkylation of Active Methylene and Related Derivatives using Alkylsilyl Peroxides by a Catalytic CuI‐DMAP System

Solvothermal Fabrication of NiO/Co3O4 Spherical Composites Modified with N‐Doped Graphene Quantum Dots as a Catalyst in the Microwave‐Assisted Synthesis of Spiro[diindenopyridine‐indoline] Triones

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K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

K₂S₂O₈‐Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl‐Substituted Indenones

Solvothermal Fabrication of NiO/Co₃O₄ Spherical Composites Modified with N‐Doped Graphene Quantum Dots as a Catalyst in the Microwave‐Assisted Synthesis of Spiro[diindenopyridine‐indoline] Triones