Palladium-Catalyzed Direct C(sp3)-H Arylation of 5H-Imidazo[2,1-a]isoindole Scaffolds With Arylbromides

被引：0
作者：
Panza, Florian [1 ]
Hauwelle, Alexandre [1 ]
Briquet, Antoine [1 ]
Awada, Ali [1 ]
Levacher, Vincent [1 ]
Hoarau, Christophe [1 ]
Baudequin, Christine [1 ]
机构：
[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA UMR6014, F-76000 Rouen, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 24期
关键词：
C-H arylation; Palladium catalysis; imidazoisoindoles; arylation; late-stage functionalization; C-H BONDS; BENZYLIC ARYLATION; ALPHA-ARYLATION; ARYL;
D O I：
10.1002/ejoc.202400058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The study of Pd(0)-catalyzed C-H bond arylation of methyl 5H-imidazo[2,1-a]isoindole-3-carboxylates with aryl bromides is reported. This methodology gives ready access to a wide range of methyl 5H-imidazo[2,1-a]isoindole-3-carboxylates that are monoarylated at their benzylic sites. The C(sp(3))-H bond arylation methodology is driven by regioselectivity under weakly basic conditions avoiding remarkably side C(sp(2))-H poly-arylation of the (hetero)aromatic unit. The process was applied to the preparation of novel imidazo[2,1-a]isoindole-based neurotransmitter Neuropeptide S antagonist analog.
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页数：5
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