Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of Catalysts and Substrate Substitution in the Synthesis of Oxindoles and β-Lactams

Impacto

Downloads

Downloads per month over past year

Solé, Daniel and Pérez-Janer, Ferran and Amenta, Arianna and Bennasar, M.-Lluïsa and Fernández López, Israel (2019) Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of Catalysts and Substrate Substitution in the Synthesis of Oxindoles and β-Lactams. Molecules, 24 (19). p. 3551. ISSN 1420-3049

[thumbnail of molecules-24-03551.pdf] PDF
Creative Commons Attribution.

6MB

Official URL: https://doi.org/10.3390/molecules24193551




Abstract

The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation states of Pd and a variety of ligands. It was found that, in the synthesis of oxindoles, ((IMes)Pd(NQ))2 can be used as an alternative to Pd2(dba)3 to catalyze the carbene CArsp2–H insertion, although it was less versatile. On the other hand, it was demonstrated that the Csp3–H insertion leading to β-lactams can be effectively promoted by both Pd(0) and Pd(II) catalysts, the latter being most efficient. Insight into the reaction mechanisms involved in these transformations was provided by DFT calculations.


Item Type:Article
Uncontrolled Keywords:palladium; diazo compounds; carbenes; oxindoles; β-Lactams; density functional calculations
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:66543
Deposited On:02 Jul 2021 14:10
Last Modified:06 Jul 2021 10:28

Origin of downloads

Repository Staff Only: item control page