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Rhodium‐Catalyzed ortho ‐Bromination of O‐Phenyl Carbamates Accelerated by a Secondary Amide‐Pendant Cyclopentadienyl Ligand
Author(s) -
Tanaka Jin,
Shibata Yu,
Joseph Anton,
Nogami Juntaro,
Terasawa Jyunichi,
Yoshimura Ryo,
Tanaka Ken
Publication year - 2020
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.202000253
Subject(s) - amide , cyclopentadienyl complex , moiety , halogenation , rhodium , chemistry , ligand (biochemistry) , medicinal chemistry , ring (chemistry) , catalysis , hydrogen bond , stereochemistry , organic chemistry , molecule , receptor , biochemistry
It has been established that a newly developed cyclopentadienyl rhodium(III) [Cp A Rh III ] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho ‐bromination of O‐phenyl carbamates with N ‐bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the Cp A ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the Cp A ligand and the carbonyl group of NBS.