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Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water
Author(s) -
Yao Yongqi,
Yang Wen,
Wang Chaoyang,
Gu Fenglong,
Yang Weitao,
Yang Dingqiao
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900033
Subject(s) - bicyclic molecule , chemistry , alkene , reagent , catalysis , adduct , radical , medicinal chemistry , organic chemistry , photochemistry , combinatorial chemistry
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 scopeof 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.