Modular Approach to Tricyclic Heterocycles through Copper Catalysis and Functionalization by Palladium‐Catalyzed C–H Arylation. Issue 18 (10th May 2017)

• Record Type: Journal Article
• Authors: Kumpulainen, Esa T. T.; Högnäsbacka, Antonia
• Is Part Of: European journal of organic chemistry. Issue 18(2013)
• Page Start: 2610
• Page End: 2614
• Publication Date: 2017-05-10
• Subjects: C–H activation -- C–C coupling -- Copper -- Heterocycles -- Palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700356
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A copper‐catalyzed Ullman reaction accompanied with oxidative C–N bond formation was used to access tricyclic heterocycles in a one‐pot operation by using atmospheric air as the terminal oxidant. This modular synthesis approach was used to synthesize previously known and novel azole‐containing heterocycles with different nitrogen position isomers. Fused heterocycles were further functionalized by palladium‐catalyzed direct C–H arylation methodology. Various electron‐rich and electron‐poor functional groups were tolerated in the ortho, meta, and para positions of the aryl bromides. Abstract : Oxidative copper‐catalyzed ring construction gives modular access to tricyclic heteroaryls. These structures are further substituted by palladium‐catalyzed C–H activation together with aryl bromides containing various functional groups.