Remote Construction of N-Heterocycles via 1,4-Palladium Shift-Mediated Double C-H Activation

Miyakoshi, Takeru and Niggli, Nadja E. and Baudoin, Olivier. (2022) Remote Construction of N-Heterocycles via 1,4-Palladium Shift-Mediated Double C-H Activation. Angewandte Chemie International Edition, 61 (17). e202116101.

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In the past years, Pd0-catalyzed C(sp3)-H activation provided efficient and step-economical methods to synthesize carbo- and heterocycles via direct C(sp2)-C(sp3) bond formation. We report herein that a 1,4-Pd shift allows access to N-heterocycles which are difficult to build via a direct reaction. It is shown that o-bromo-N-methylanilines undergo a 1,4-Pd shift at the N-methyl group, followed by intramolecular trapping by C(sp2)-H or C(sp3)-H activation at another nitrogen substituent and remote C-C bond formation to generate biologically relevant isoindolines and β-lactams. The product selectivity is influenced by the employed ligand, with NHCs favoring the product of remote C-C coupling against products arising from direct C-C coupling and N-demethylation.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:02 Nov 2022 07:16
Deposited On:02 Nov 2022 07:16

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