Multicomponent Synthesis of Isoindolinone Frameworks via Rh III ‐Catalysed in situ Directing Group‐Assisted Tandem Oxidative Olefination/Michael Addition | Zendy

Wang Liang | Zendy; Liu Xi | Zendy; Liu Jianbiao | Zendy; Shen Jun | Zendy; Chen Qun | Zendy; He Mingyang | Zendy

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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.

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