A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles

• Published in: Advanced synthesis & catalysis Vol. 354; no. 11-12; pp. 2123 - 2128
• Main Authors: Huang, Dayun, Chen, Jiuxi, Dan, Weixing, Ding, Jinchang, Liu, Miaochang, Wu, Huayue
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 13-08-2012; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: 2-bromo-3-arylthioindoles; 3-arylthioindoles; bromosulfenylation; Catalysis; Chemistry; Derivatives; Disulfides; Exact sciences and technology; Functional groups; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Indoles; metal-free conditions; Organic chemistry; Preparations and properties; Stability; sulfenylation; Synthesis; Tolerances; One pot reaction; Nitrogen heterocycle; Sulfenylation; Organic bromine compounds; 2-bromo-3-arylthioindoles; Organic disulfide; metal-free conditions; bromosulfenylation; 3-arylthioindoles; Bromine Organic compounds; Indole derivatives; Chemical synthesis; Functional group
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201200227

An efficient metal‐free sulfenylation of indoles with disulfides has been developed, leading to 3‐arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2‐bromo‐3‐arylthioindole derivatives in good yield by the one‐pot construction of CS and CBr bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.