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Direct methyl C(sp3)–H azolation of thioanisoles via oxidative radical coupling

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Abstract

A method for metal-free, 1,3-dibromo-5,5-dimethylhydantoin mediated methyl C(sp3)–H bond azolation of thioanisoles has been developed, affording a facile route for the construction of nitrogen-functionalized thioanisoles, possibly via a nitrogen-centered radical process. This reaction represents an important addition to the limited number of existing methods for the methyl C(sp3)–H bond functionalization of thioanisoles, and may find practical application in the synthesis of nitrogen-alkylated azoles.

Graphical abstract: Direct methyl C(sp3)–H azolation of thioanisoles via oxidative radical coupling

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Publication details

The article was received on 10 Jul 2019, accepted on 15 Aug 2019 and first published on 15 Aug 2019


Article type: Communication
DOI: 10.1039/C9OB01530B
Org. Biomol. Chem., 2019, Advance Article

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    Direct methyl C(sp3)–H azolation of thioanisoles via oxidative radical coupling

    X. Wang, C. Li, Y. Zhang, B. Zhang and K. Sun, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01530B

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