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

Angewandte Chemie (International ed. in English) (2020-07-22)
Tomáš Čarný, Ronan Rocaboy, Antonin Clemenceau, Olivier Baudoin
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 β-carbon atom. Mechanistic studies showed that the aminocarbonylation of the σ-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.

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Sigma-Aldrich
Cesium pivalate, 98%