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Chelation‐Assisted Nickel‐Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction
Author(s) -
Misal Castro Luis C.,
Obata Atsushi,
Aihara Yoshinori,
Chatani Naoto
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504596
Subject(s) - alkyne , catalytic cycle , chemistry , catalysis , annulation , nickel , amide , regioselectivity , quinoline , oxidative addition , medicinal chemistry , combinatorial chemistry , organic chemistry
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.