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In recent years, the transition metal-free sulfenylation of C--H bond for C--S formation has been rapidly advanced and has become an eco-friendly synthetic tool for pharmacists and organic chemists. Various natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds, alkanes, have been employed for sulfenylating reactions. This review will focus on the recent five-year advances in C--S bond formation via direct sulfenylation of C(sp3)--H bonds under metal-free conditions and elaborate their mechanisms from a new perspective.