Aerobic Acyloxylation of Allylic C-H Bonds Initiated by a Pd

Autor: Caitlin V, Kozack, Jennifer A, Sowin, Jonathan N, Jaworski, Andrei V, Iosub, Shannon S, Stahl
Rok vydání: 2019
Předmět:
Zdroj: ChemSusChem
ISSN: 1864-564X
Popis: Palladium-catalyzed allylic C–H oxidation has been widely studied, but most precedents use acetic acid as the coupling partner. Here, we report a method compatible with diverse carboxylic acid partners. Use of a Pd(0) pre-catalyst under aerobic reaction conditions leads to oxidation of Pd(0) by O(2) in the presence of the desired carboxylic acid to generate a Pd(II) dicarboxylate that promotes acyloxylation of the allylic C–H bond. Good-to-excellent yields are obtained with ~1:1 ratio of the alkene and carboxylic acid reagents. Optimized reaction conditions employ 4,5-diazafluoren-9-one (DAF) as a ligand, in combination with a quinone/Fe(phthalocyanine) cocatalyst system to support aerobic catalytic turnover.
Databáze: OpenAIRE