A relative synthetic strategy toward intermolecular oxidative C−Chalcogen bond formation of alkanes has been illustrated using both Cu(II) assisted 𝑣𝑠 Cu(II) free conditions. This led to construction of a comparative study of hydrocarbon benzylic and 2°/3°-cycloalkyl moieties bond sulfenylation and selenation protocol by the chalcogen sources, particularly sulfur and selenium, respectively. In addition, this protocol disclosed the auspicious formation of sp3C−S coupling products over leading the sp3C−N coupling products by using 2-mercaptobenzothiazole (MBT) substrates.
