Chelation‐Assisted Nickel‐Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction. Issue 4 (21st December 2015)

• Record Type: Journal Article
• Authors: Misal Castro, Luis C.; Obata, Atsushi; Aihara, Yoshinori; Chatani, Naoto
• Is Part Of: Chemistry. Volume 22:Issue 4(2016)
• Page Start: 1362
• Page End: 1367
• Publication Date: 2015-12-21
• Subjects: alkynes -- aromatic homologation -- C−H activation -- chelate-assistance -- nickel; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201504596
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A nickel/NHC system for regioselective oxidative annulation by double C−H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8‐aminoquinoline, embedded in the substrate. Various 5, 6, 7, 8‐tetrasubstituted‐ N ‐(quinolin‐8‐yl)‐1‐naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni 0 /Ni II catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor. Abstract : In two shakes : Oxidative annulation by a double C−H activation/alkyne insertion reaction was achieved by a nickel/NHC system. A Ni 0 /Ni II catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.