Advances in free-radical alkylation and arylation with organoboronic acids

Herein, we report the synthesis of functionalized dihydro-benzo[b]fluorenones through a manganese-mediated cascade radical cyclization of β-alkynyl propenones [1,6-enynes] with arylboronic acids. In the present strategy, the in-situ generated aryl radical undergoes chemo-selective addition followed by 5exo-trig cyclization. The reaction is emphasized by high atom-and step-economy with the construction of three new CÀ C bonds to access the dihydrobenzo[b]fluorenones in 68-81% yield under mild reaction conditions. The synthetic efficacy of the developed method is evidenced by the construction of new CÀ C and CÀ N bonds.

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Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Reddy

Kajare

Punna

2022

Adv Synth Catal

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Catalyst‐Free, Air‐Mediated C(sp²)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids

Zhang,

Li,

Liao

et al. 2023

Adv Synth Catal

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The air mediated radical alkylation of cyclic aldimines via autoxidation of alkylboronic acids has been realized under mild reaction conditions. By simply heating cyclic aldimines with alkylboronic acid using air as sole oxidant, this protocol provides a catalyst‐free access to a variety of alkylated cyclic aldimines with 21–91% yields. Preliminary mechanistic studies suggest that a radical pathway might be involved in the reaction.

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Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds

Li,

Tanaka,

Imagawa

et al. 2023

Chemistry A European J

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The cycloaddition of nitrile oxides with ethynyl‐B(dan) (dan=naphthalene‐1,8‐diaminato) allowed the facile preparation of diverse isoxazolyl‐B(dan) compounds, all of which displayed excellent protodeborylation‐resistant properties. The dan‐installation on the boron center proves vital to the high stability of the products as well as the perfect regioselectivity arising from hydrogen bond‐directed orientation in the cycloaddition. The diminished boron‐Lewis acidity of ethynyl‐B(dan) also renders it amenable to azide‐alkyne cycloaddition, Larock indole synthesis and related heteroannulations. The obtained boron‐containing triazole, indoles, benzofuran and indenone exhibit sufficient resistance toward protodeborylation. Despite the commonly accepted transmetalation‐inactive property derived from the diminished Lewis acidity, the synthesized heteroaryl‐B(dan) compound was still found to be convertible to the oligoarene via sequential Suzuki‐Miyaura coupling.

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Advances in free-radical alkylation and arylation with organoboronic acids

Abstract: Organoboronic acids act as carbon-centered radical precursors that are widely utilized to construct diverse C-C bonds. This review summarizes the advances in this field. It contains four parts of content...

Cited by 7 publications

References 65 publications

Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Catalyst‐Free, Air‐Mediated C(sp²)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids

Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds

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Advances in free-radical alkylation and arylation with organoboronic acids

Abstract: Organoboronic acids act as carbon-centered radical precursors that are widely utilized to construct diverse C-C bonds. This review summarizes the advances in this field. It contains four parts of content...

Cited by 7 publications

References 65 publications

Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Catalyst‐Free, Air‐Mediated C(sp2)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids

Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds

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Product

Resources

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Catalyst‐Free, Air‐Mediated C(sp²)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids