Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts as S-arylation sources. Issue 21 (18th May 2020)

• Record Type: Journal Article
• Authors: Li, Jianxiao; Tang, Hao; Lin, Zidong; Yang, Shaorong; Wu, Wanqing; Jiang, Huanfeng
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 21(2020)
• Page Start: 4071
• Page End: 4078
• Publication Date: 2020-05-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00828a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel palladium-catalyzed three-component cascade arylthiolation for the assembly of 3-sulfenylindoles and 3-sulfenylbenzofurans is described, with aryldiazonium salts as the ideal S -arylation sources. Abstract : A novel and efficient palladium-catalyzed three-component cascade cyclization/arylthiolation has been developed for the assembly of diverse 3-sulfenylindole and 3-sulfenylbenzofuran derivatives from 2-alkynylamines and 2-alkynylphenols, aryldiazonium salts, and Na2 S2 O3 under aerobic conditions with PEG-200 as an environmentally benign medium. The current study features exceptional functional group tolerance without additional ligands, oxidants or silver salts, and eco-friendly mild reaction conditions. The ionic liquid [C2 OHmim]Cl plays a crucial role in this protocol as an environmentally friendly additive. Notably, this procedure represents the first example of the use of aryldiazonium salts as direct S -arylation sources in this type of chemical transformation.