Journal
ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02523
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Funding
- National Natural Science Foundation of China [22101066]
- Science and Technology Plan of Shenzhen [JCYJ20210324133001004, JCYJ20210324132803009]
- Natural Science Foundation of Guangdong [2020A1515010564, 2022A1515010863]
- Guang-dong Basic and Applied Basic Research Foundation [2021A1515220069]
- Talent Plan of the Pearl River in Guangdong
- Guangdong Province Covid-19 Pandemic Control Research Fund [2020KZDZX1218]
- State Key Laboratory of Urban Water Resource and Environment (Harbin Institute of Technology) [2022TS23]
- Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University
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We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for remote C(sp(3))-H functionalization reaction, including cyanation, oxidation, and etherification. This method efficiently constructs structurally diverse gamma-cyano, gamma-carbonyl, and gamma-oxygenated alkenes with excellent stereoselectivity.
We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for the remote C(sp(3))-H functionalization reaction, which includes cyanation, oxidation, and etherification under visible-light-induced photochemical conditions. This reaction is achieved using readily available alkyl N-hydroxyphthalimide esters as radical precursors, which can efficiently react with diverse alkynes to form key vinyl radical intermediates followed by a 1,5-HAT process. A series of structurally diverse gamma-cyano, gamma-carbonyl, and gamma-oxygenated alkenes with excellent stereoselectivity can be efficiently constructed by this synthetic protocol.
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