Journal
CHEMSUSCHEM
Volume 12, Issue 13, Pages 3003-3007Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201900727
Keywords
acyloxylation; aerobic oxidation; C-H activation; homogeneous catalysis; palladium
Funding
- Division of Chemistry [DGE-1256259, CHE-1665120] Funding Source: Medline
- NIH HHS [S10 OD020022] Funding Source: Medline
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Palladium-catalyzed allylic C-H oxidation has been widely studied, but most precedents use acetic acid as the coupling partner. In this study, a method compatible with diverse carboxylic acid partners has been developed. Use of a Pd-0 precatalyst 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 a roughly 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/iron phthalocyanine cocatalyst system to support aerobic catalytic turnover.
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