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Rh III ‐Catalyzed Directed C−H Bromination and Iodination to Synthesize Atropisomeric Biaryls
Author(s) -
Kim Kiseong,
Hyun Jaeyong,
Kim Jin,
Kim Hyunwoo
Publication year - 2016
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.201600259
Subject(s) - halogenation , chemistry , pivalic acid , atropisomer , catalysis , aryl , medicinal chemistry , dichloroethane , cyclohexane , organic chemistry , alkyl
The [Rh III Cp*]‐catalyzed directed C−H bromination and iodination reactions of 2‐aryl isoquinolines/pyridines are highly efficient and afford atropisomeric biaryl compounds (Cp*=1,2,3,4,5‐pentamethylcyclopenta‐2,4‐dienyl) in good yields. Among several reported C−H bond halogenation methods, the combination of [Rh III Cp*Cl 2 ] 2 /AgSbF 6 , N ‐halosuccinimide, and pivalic acid in 1,2‐dichloroethane is found to be the only effective catalytic system to provide atropisomeric 2′‐halogenated 2‐aryl isoquinolines/pyridines.