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Issue 15, 2018
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An I2-mediated aerobic oxidative annulation of amidines with tertiary amines via C–H amination/C–N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines

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Abstract

An iodine-mediated formal oxidative cycloaddition of amidines with tertiary amines was first demonstrated in air. Both symmetrical and unsymmetrical 2,4-disubstituted 1,3,5-triazines were obtained in up to 85% yields. It is noted that a tertiary amine was employed as a one carbon synthon of 1,3,5-triazines and two C–N bonds were formed in one pot. Control experiments revealed that the reaction underwent a radical pathway promoted by I+. The method is transition-metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates.

Graphical abstract: An I2-mediated aerobic oxidative annulation of amidines with tertiary amines via C–H amination/C–N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines

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Publication details

The article was received on 14 Mar 2018, accepted on 23 Mar 2018 and first published on 24 Mar 2018


Article type: Communication
DOI: 10.1039/C8OB00635K
Citation: Org. Biomol. Chem., 2018,16, 2629-2633
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    An I2-mediated aerobic oxidative annulation of amidines with tertiary amines via C–H amination/C–N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines

    Y. Yan, Z. Li, C. Cui, H. Li, M. Shi and Y. Liu, Org. Biomol. Chem., 2018, 16, 2629
    DOI: 10.1039/C8OB00635K

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