A novel, efficient and unprecedented green protocol for the formation of C-S bond has been developed under metal-free conditions. This protocol involves the synthesis of aryl sulfides through the cross-dehydrogenative coupling of readily available aryl thiols with electron-rich species under 10 solvent-free conditions and the corresponding aryl sulfides are obtained in high to quantitative yields. A catalytic amount of inexpensive and non-toxic iodine drives the reaction and no exclusion of air and expensive ligands are required.

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An unprecedented diacetoxyiodobenzene induced direct arylation of guaiacol derivatives and electron-rich arenes using a Lewis acid as an activator furnishes unsymmetrical biaryls without prefunctionalization of both coupling partners. The addition of electron-rich arenes on the α-position of electrophilic masked o-benzoquinones in an anti-Michael addition fashion affords the highly oxygenated unsymmetrical biaryls in good to excellent yields.

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