Visible Light Induced C2 Alkylation of 2<i>H</i>‐Benzoxazoles with Cycloalkanes and Ethers <i>via</i> Selectfluor‐Mediated Oxidation

Chen, Bin; Huang, Zhen; Hu, Zhigang; Liu, Xinghai; Weng, Jian‐Quan

doi:10.1002/slct.202204773

ChemistrySelect

2023

DOI: 10.1002/slct.202204773

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Visible Light Induced C2 Alkylation of 2H‐Benzoxazoles with Cycloalkanes and Ethers via Selectfluor‐Mediated Oxidation

Bin Chen

Zhen Huang

Zhigang Hu

et al.

Abstract: An efficient selectfluor-oxidative protocol was developed for the direct C2-alkylation of 2H-benzoxazoles with cycloalkanes and ethers. Selectfluor can effectively promote the oxidative cross-coupling without an external catalyst under the visible light irradiation at room temperature. This alkylation reaction tolerates a wide range of functional groups affording 48 examples of the C2-alkylated 2H-benzoxazoles in moderate to good yields.

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2024

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Cited by 2 publications

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Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Grishin,

Mulina,

et al. 2024

Asian J Org Chem

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The use of C‐H compounds as reactive partners in a variety of transformations represents the state of the art in synthetic methodology. In this review, we have summarized the main achievements in using ethers as building blocks for the construction and modification of one of the basic platforms of organic chemistry, nitrogen‐containing heterocycles. Ethers, previously considered mainly as solvents, are excellent CH‐partners, capable of generating radical or cationic reactive species under the action of HAT agents and oxidants. The challenge in this field is the still limited number of heterocyclic systems and other starting reagents, with which the processes can be carried out selectively due to closer bond dissociation energies and oxidation potentials of heterocycles, reactive intermediates and ethers. However, the fine‐tuning of the reaction system using electro‐ and photochemical approaches and a deep understanding of the reaction pathways make the use of ethers as C‐H reagents a promising synthetic strategy.

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Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Grishin,

Mulina,

et al. 2024

Asian J Org Chem

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Photo-Induced α-Oxyalkylation of Aryl Chlorides with Ethers and Alcohols through Homolytic Aromatic Substitution

Shirakawa,

Aoki,

Yonekura

et al. 2024

Synthesis

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The α-oxyalkylation of aryl chlorides with ethers and alcohols using a small amount of a peroxide was found to be induced by photoirradiation. The reaction proceeds through a homolytic aromatic substitution (HAS) mechanism consisting of addition of an α-oxyalkyl radical to an aryl chloride and elimination of the chlorine atom to give the α-oxyalkylation product, where photoirradiation is considered to effect not only the initiation step to facilitate homolysis of a peroxide, but also the propagating radical chain.

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Visible Light Induced C2 Alkylation of 2H‐Benzoxazoles with Cycloalkanes and Ethers via Selectfluor‐Mediated Oxidation

Cited by 2 publications

References 48 publications

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Photo-Induced α-Oxyalkylation of Aryl Chlorides with Ethers and Alcohols through Homolytic Aromatic Substitution

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