Gold‐Catalyzed Reaction of Anthranils with Alkynyl Sulfones for the Regioselective Formation of 3‐Hydroxyquinolines. Issue 7 (10th March 2022)

• Record Type: Journal Article
• Authors: Wu, Yufeng; Hu, Chao; Wang, Tao; Eberle, Lukas; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 7(2022)
• Page Start: 1233
• Page End: 1238
• Publication Date: 2022-03-10
• Subjects: anthranils -- alkynyl sulfones -- gold catalysis -- 3-hydroxyquinoline -- chemoselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202101469
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The gold‐catalyzed regioselective formation of 3‐hydroxyquinoline is accessed by combining anthranils and alkynyl sulfones. The selective scission of the epoxide intermediate stems from the thermodynamic stability difference of the resultant cation according to quantum chemical calculations. The subsequent semi‐pinacol rearrangement leads to the 1, 2‐shift of an aryl or alkyl group originating from the sulfone. A gram‐scale synthesis of 3‐hydroxyquinoline further manifests the viability of the protocol for the preparation of this important scaffold. Abstract :