期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 10, 页码 5189-5192出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202015054
关键词
[3+2] annulation; C-H activation; palladium; site selectivity
资金
- MEXT [17H06091]
- Naito Foundation
- China Scholarship Council [CSC201908050207]
The palladium-catalyzed [3+2] annulation of aromatic amides with maleimides via the activation of ortho benzylic C-H and meta C-H bonds is reported, with a key role played by the presence of a 2-methylthiophenyl directing group for the success of the reaction. The irreversible cleavage of these C-H bonds leads to the formation of five-membered cyclic products.
The palladium-catalyzed [3+2] annulation of aromatic amides with maleimides via the activation of ortho benzylic C-H and meta C-H bonds is reported. Carboxamide and anilide type substrates that contain a 2-methylthiophenyl group both participate in this [3+2] annulation, indicating that the presence of a 2-methylthiophenyl directing group is a key for the success of the reaction. The first C-H bond activation at the benzylic C-H bond is followed by a second C-H bond activation at the meta C-H bond to give five-membered cyclic products. The cleavage of these C-H bonds is irreversible.
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