Premium
Multicomponent Synthesis of Isoindolinone Frameworks via Rh III ‐Catalysed in situ Directing Group‐Assisted Tandem Oxidative Olefination/Michael Addition
Author(s) -
Wang Liang,
Liu Xi,
Liu Jianbiao,
Shen Jun,
Chen Qun,
He Mingyang
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800120
Subject(s) - chemoselectivity , chemistry , tandem , functional group , denticity , catalysis , in situ , aryl , cascade reaction , combinatorial chemistry , medicinal chemistry , stereochemistry , alkyl , organic chemistry , materials science , polymer , crystal structure , composite material
A Rh III ‐catalysed three‐component synthesis of isoindolinone frameworks via direct assembly of benzoyl chlorides, o ‐aminophenols and activated alkenes has been developed. The process involves in situ generation of o ‐aminophenol (OAP)‐based bidentate directing group (DG), Rh III ‐catalysed tandem ortho C−H olefination and subsequent cyclization via aza‐Michael addition. This protocol exhibits good chemoselectivity and functional group tolerance. Computational studies showed that the presence of hydroxyl group on the N ‐aryl ring could enhance the chemoselectivity of the reaction.