Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 4, Pages 506-513Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900033
Keywords
radical addition; alkenes; water chemistry; density functional calculations
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Funding
- National Key Research and Development Program of China [2017YFB0203403]
- National Natural Science Foundation of China [21172081, 21372090, 21673085]
- Natural Science Foundation of Guangdong Province [S2013020013091]
- City of Guangzhou Science and Technology Plan Projects [201510010054]
- Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme
- leading talent project of Guangdong Province
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An air-promoted radical addition reaction of various thiols to oxa(aza)bicyclic alkenes is reported, leading to the corresponding exo adducts in good to excellent yields (up to 99%) in water without the use of any metal catalyst, photoredox catalyst or radical initiator reagent under mild conditions. The reaction has a wide scope of oxa(aza)bicyclic alkenes and thiols, which provides an easy and clean way for the direct preparation of thioethers. A proposed mechanism of an exo free radical attacking the double bond of an oxa(aza)bicyclic alkene was investigated by DFT calculations of stepwise reaction pathways and control experiments.
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