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

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.