Iodine-catalyzed intermolecular 1,2-thio (seleno)amination of alkenes with 1,2,3-triazoles and disulfides (diselenides) in air

Ji, Jian; Chen, Xuwen; Hu, Zongjing; Guan, Cong; Liu, Jinhua; Deng, Yaqi; Liu, Shunying

doi:10.1039/d4qo00246f

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00246f

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Iodine-catalyzed intermolecular 1,2-thio (seleno)amination of alkenes with 1,2,3-triazoles and disulfides (diselenides) in air

Jian Ji,

Xuwen Chen,

Zongjing Hu

et al.

Abstract: Iodine-catalyzed 1,2-thio (seleno)amination of alkenes via direct N- and C-centered radical cross-coupling was established to elicit highly regioselective β-triazolized thioalkyl compounds.

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Iodide Ion-Promoted Highly Regioselective Triazolization of Aldehydes via Desulfonation-Associated Direct Radical Coupling

Deng,

Wei,

Xue

et al. 2024

J. Org. Chem.

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A highly efficient iodide ion (I − )-promoted method for direct α-C(sp 2 )−H triazolization of aldehydes has been developed for the regioselective synthesis of N 2 -substituted triazole derivatives. The developed method features the corresponding products in good yields (up to 99%) with an excellent functional group tolerance via an intermolecular oxidative radical coupling. Experimental mechanistic investigations indicate that the reaction proceeds via an I − -promoted synergistic desulfonylation process, which provides a high regioselectivity. The developed method provides a direct, metal-free, operationally simple, and highly regioselective approach to C(sp 2 )−H triazolization from easily accessible aldehydes in air.

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Iodide Ion-Promoted Highly Regioselective Triazolization of Aldehydes via Desulfonation-Associated Direct Radical Coupling

Deng,

Wei,

Xue

et al. 2024

J. Org. Chem.

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show abstract

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Iodine-catalyzed intermolecular 1,2-thio (seleno)amination of alkenes with 1,2,3-triazoles and disulfides (diselenides) in air

Abstract: Iodine-catalyzed 1,2-thio (seleno)amination of alkenes via direct N- and C-centered radical cross-coupling was established to elicit highly regioselective β-triazolized thioalkyl compounds.

Cited by 1 publication

References 34 publications

Iodide Ion-Promoted Highly Regioselective Triazolization of Aldehydes via Desulfonation-Associated Direct Radical Coupling

Iodide Ion-Promoted Highly Regioselective Triazolization of Aldehydes via Desulfonation-Associated Direct Radical Coupling

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