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Construction of Biaryl Scaffolds from Iodoarenes and C−H Heteroarenes Using an Amide Base Generated in situ from Aminosilane and Fluoride Anion
Author(s) -
Shigeno Masanori,
Kai Yusuke,
Yamada Tetsuya,
Hayashi Kazutoshi,
NozawaKumada Kanako,
Denneval Charline,
Kondo Yoshinori
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.201800438
Subject(s) - chemistry , phenazine , pyrazine , amide , homolysis , fluoride , electron paramagnetic resonance , reactivity (psychology) , phenoxazine , tetramethylammonium , base (topology) , aryl radical , photochemistry , in situ , ion , medicinal chemistry , radical , organic chemistry , aryl , inorganic chemistry , alkyl , medicine , mathematical analysis , physics , alternative medicine , mathematics , nuclear magnetic resonance , pathology , phenothiazine , pharmacology
Iodoarenes and C−H heteroarenes are coupled to form a biaryl in the presence of an amide base generated in situ from tetramethylammonium fluoride (TMAF) and hexamethyldisilazane (HMDS) by homolytic aromatic substitution (HAS). This reaction can be used with electron‐rich, ‐deficient, and ortho ‐substituted haloarenes. Both electron‐rich and ‐deficient C−H heteroarenes can also be utilized. Involvement of a radical intermediate was confirmed by radical inhibition experiments, deuterium‐labelling experiments, and EPR spectral measurements. Enhancement of the reactivity of electron‐rich N ‐methylpyrrole was observed in the presence of electron‐poor phenazine or pyrazine.