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Synthesis of Amides and Esters by Palladium(0)-Catalyzed Carbonylative C(sp3)-H Activation

Carny, Tomas and Rocaboy, Ronan and Clemenceau, Antonin and Baudoin, Olivier. (2020) Synthesis of Amides and Esters by Palladium(0)-Catalyzed Carbonylative C(sp3)-H Activation. Angewandte Chemie International Edition, 59 (43). pp. 18980-18984.

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Abstract

The 1,4-palladium shift strategy allows the functionalization of remote C-H bonds that are difficult to reach directly. Reported here is a domino reaction proceeding by C(sp3)-H activation, 1,4-palladium shift, and amino- or alkoxycarbonylation, which generates a variety of amides and esters bearing a quaternary beta-carbon atom. Mechanistic studies showed that the aminocarbonylation of the sigma-alkylpalladium intermediate arising from the palladium shift is fast using PPh3 as the ligand, and leads to the amide rather than the previously reported indanone product.
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
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
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Last Modified:13 Oct 2020 07:46
Deposited On:14 Sep 2020 13:54

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