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Iron‐Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes
Author(s) -
Ilies Laurean,
Arslanoglu Yasin,
Matsubara Tatsuaki,
Nakamura Eiichi
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800200
Subject(s) - chemistry , alkyne , catalysis , naphthalene , annulation , denticity , lewis acids and bases , conjugated system , halide , medicinal chemistry , combinatorial chemistry , organic chemistry , metal , polymer
The iron/diphosphine‐catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 °C to produce a variety of indenone derivatives. The reaction proceeds through iron‐catalyzed C−H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic Zn II . The reaction of naphthalene and anthraceneamide yields π‐conjugated indenone derivatives.