Visible‐Light Mediated Tandem Oxidation–Organocatalyzed Aromatic C−S Bond Functionalization: Synthesis of 2‐(Benzo[b]thiophen‐2‐yl)benzenesulfonamide Derivatives

• Published in: European journal of organic chemistry Vol. 27; no. 17
• Main Authors: Venkateswarlu, Derangula, Murugesh, Venkatesh, Sridhar, Balasubramanian, Prakash Singh, Surya
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 03.05.2024; Wiley Subscription Services, Inc
• Subjects: Amines; aromatic sulfides; Chemistry; Chemistry, Organic; C−S bond functionalization; organocatalysis; Oxidation; Physical Sciences; Science & Technology; Sulfones; tandem; organocatalysis; TRIARYLSULFONIUM SALTS; ACTIVATION; C-S bond functionalization; tandem; oxidation; aromatic sulfides
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202301187

Herein, we demonstrated a visible light mediated tandem oxidation–organo catalyzed C−S bond functionalization protocol for the cleavage of aromatic C−S bond. The investigation encompassed the functionalization of C−S bonds within sulfones, sulfoxides, and aliphatic sulfide derivatives. However, the process of functionalizing the C−S bond in aromatic sulfides remains uncertain. The presented protocol demonstrates the C−S bond functionalization on benzo[b]benzo[4,5]thieno[2,3‐d]thiophene derivative and amines including primary and secondary amines as well. A radical mediated mechanism was proposed for the tandem oxidation–organocatalyzed C−S bond functionalization protocol. Visible light mediated tandem oxidation–organo catalyzed C−S bond functionalization protocol for the cleavage of aromatic C−S bond. The investigation encompassed the functionalization of C−S bonds within sulfones, sulfoxides, and aliphatic sulfide derivatives. However, the process of functionalizing the C−S bond in aromatic sulfides remains uncertain. The presented protocol demonstrates the C−S bond functionalization on benzo[b]benzo[4,5]thieno[2,3‐d]thiophene derivative and amines including primary and secondary amines as well.