Heteroaryl 2-sulfonamides are an important structural moiety in drug discovery. However, reports of the efficient synthesis of these scaffolds are rare. Herein we disclose new reaction conditions to synthesize heteroaryl 2-sulfonamides from disulfanes and amines through an SN2–oxidation cascade. The approach is compatible with a wide variety of heteroaryl and amine substrates and can be conducted on a gram scale. A potential Werner Syndrome Protein (WRN) small molecule inhibitor H3B-968 was also synthesized by this method.