Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5090-5093Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01806
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Funding
- National Program on Key Research Project [2016YFA0602900]
- National Natural Science Foundation of China [21420102003]
- Fundamental Research Funds for the Central Universities [2015ZY001]
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A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
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