Journal
CCS CHEMISTRY
Volume 4, Issue 4, Pages 1190-1198Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202100944
Keywords
alkene difunctionalization; olefination; migration; fluoroalkyl; radical reactions
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Funding
- National Natural Science Foundation of China [21971173]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201905]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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We have described a novel and efficient radical-mediated intermolecular fluoroalkylative olefination of unactivated alkenes. This transformation involved a radical docking-migration cascade, utilizing strategically designed dual-function alkenylating reagents to generate vinylated products with exclusive E-configuration. The reaction demonstrated mild conditions, wide functional group compatibility, and unique chemo-, regio-, and stereoselectivities. Moreover, this protocol has provided a valuable approach for the late-stage olefination of complex natural products and drug derivatives containing alkenyl moieties.
We have disclosed a novel, efficient radical-mediated intermolecular fluoroalkylative olefination of unactivated alkenes. The transformation proceeded through a radical docking-migration cascade, in which a portfolio of strategically designed dual-function alkenylating reagents was harnessed to afford vinylated products with exclusive E-configuration. The reaction featured mild conditions, broad functional group compatibility, and unique chemo-, regio-, and stereoselectivities. The protocol has also provided a useful approach for late-stage olefination of complex natural products and drug derivatives containing alkenyl moieties. [GRAPHICS] .
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