Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 7852-7859Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00729
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Funding
- National Natural Science Foundation of China [21372265]
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The copper(II)-promoted free-radical oxidative di-functionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by O-18-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.
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