Premium
Palladium‐Catalyzed C–C Coupling/C–H Activation: Formation of Isoindolinone‐Fused Heterocyclic Compounds
Author(s) -
Hu Yimin,
Ren Dong,
Zhang Lidong,
Lin Xiangang,
Wan Jing
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000492
Subject(s) - chemistry , aryl , palladium , regioselectivity , iodobenzene , halide , isomerization , moiety , catalysis , coupling reaction , combinatorial chemistry , cascade reaction , sulfonyl , medicinal chemistry , organic chemistry , alkyl
Inactivated dienes containing a cycloalkenyl moiety with aryl halides were used in a palladium‐catalyzed reaction to give different kinds of rare, fused isoindolinone heterocyclic compounds through highly regioselective C–C coupling/C–H functionalization in a one‐step domino reaction. Different dienes and aryl halides were shown to be very active in this reaction. Substituents on the aryl halides were ethoxycarbonyl, methoxycarbonyl, sulfonyl, formacyl, keto, cyano,acetyl, and naphthalene. The C–H functionalization and allyl isomerization occurred simultaneously when 1‐iodobenzene or aryl halides were treated with substrates having allylmoieties on the protecting group. The generality of this process makes the reaction highly valuable due to the synthetic and medicinal importance of these kinds of fused heterocycles.