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Allylic C–H Acetoxylation with a 45-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy to Achieve Aerobic Catalytic Turnover

机译:烯丙基C-H乙酰氧基与45- Diazafluorenone结扎钯催化剂:配体为基础的策略实现有氧催化周转

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摘要

Pd-catalyzed C–H oxidation reactions often require the use of oxidants other than O2. Here, we demonstrate a ligand-based strategy to replace benzoquinone with O2 as the stoichiometric oxidant in Pd-catalyzed allylic C–H acetoxylation. Use of 4,5-diazafluorenone (>1) as an ancillary ligand for Pd(OAc)2 enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields and selectivity under 1 atm O2. Mechanistic studies reveal that >1 facilitates C–O reductive elimination from a π-allyl-PdII intermediate, thereby eliminating the requirement for benzoquinone in this key catalytic step.

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