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Iridium‐Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product
Author(s) -
Yamane Shintaro,
Hinoue Tomoaki,
Usuki Yoshinosuke,
Itazaki Masumi,
Nakazawa Hiroshi,
Hayashi Yoshihiro,
Kawauchi Susumu,
Miura Masahiro,
Satoh Tetsuya
Publication year - 2018
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.201801245
Subject(s) - iridium , decarbonylation , chemistry , rhodium , catalysis , benzofuran , aldehyde , metallacycle , photochemistry , medicinal chemistry , organic chemistry , physics , x ray crystallography , diffraction , optics
The iridium(III)/copper(II)‐catalyzed dehydrogenative coupling of salicylaldehydes with internal alkynes proceeds efficiently under atmospheric oxygen through aldehyde C−H bond cleavage and decarbonylation. A variety of benzofuran derivatives can be synthesized by the environmentally benign procedure. DFT calculations suggest that this unique transformation involves the facile deinsertion of CO in the key metallacycle intermediate, which is in marked contrast to the corresponding rhodium(III) catalysis that leads to CO‐retentive chromone derivatives.