Visible‐Light Photoredox‐Catalyzed Cross‐Dehydrogenative Coupling of Tetrahydroisoquinolines with 3‐Fluorooxindoles. Issue 8 (26th July 2019)

• Record Type: Journal Article
• Authors: Ji, Jian; Chen, Ling‐Yan; Qiu, Zi‐Bin; Ren, Xinfeng; Li, Ya
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 8(2019)
• Page Start: 1436
• Page End: 1440
• Publication Date: 2019-07-26
• Subjects: diastereoselectivity -- 3-fluorooxindoles -- photocatalysis -- tetrahydroisoquinolines -- visible light; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900378
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The 3‐fluorooxindole and tetrahydroisoquinoline scaffolds are both important structures because of their associated biological and pharmaceutical activities. Herein, we report a highly diastereoselective synthesis of 3‐fluorooxindoles fully substituted at the 3‐position and containing a tetrahydroisoquinoline fragment, through the visible‐light photoredox‐catalyzed cross‐dehydrogenative coupling of tetrahydroisoquinolines with 3‐fluorooxindoles. The protocol featured a wide substrate scope: N‐alkyl‐, N‐haloalkyl‐, N‐aryl‐, N‐allyl‐, N‐propargyl‐, and NH 3‐fluorooxinloles were all able to be used to form the desired coupling products in up to 92% yield and 99 : 1 anti/syn . Abstract : A highly diastereoselective synthesis of 3‐fluorooxindoles, fully substituted at the 3‐position and containing a tetrahydroisoquinoline fragment, was achieved through the visible‐light photoredox‐catalyzed cross‐dehydrogenative coupling of tetrahydroisoquinolines with 3‐fluorooxindoles.