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Synthesis of 6-Fluoroalkyl 6H-Benzo[c]chromenes via Visible-Light-Promoted Radical Addition/Cyclization of Biaryl Vinyl Ethers

Author:
Deng, Qinfei, Tan, Liping, Xu, Yan, Liu, Ping, Sun, Peipei
Source:
Journal of organic chemistry 2018 v.83 no.11 pp. 6151-6161
ISSN:
1520-6904
Subject:
aromatic compounds, cyclization reactions, ethers, free radicals, moieties, organic chemistry, protocols
Abstract:
A novel visible-light-promoted cascade cyclization reaction for the synthesis of 6-fluoroalkyl 6H-benzo[c]chromenes has been successfully realized, which was initiated by intermolecular radical addition to biaryl vinyl ethers using easily available fluoroalkylated reagents BrCF₂CO₂Et or 2-bromo-2,2-difluoroamides as the sources of fluorinated radicals, followed by the cyclization onto an aromatic ring process. This protocol tolerated a wide range of functional groups and provided the desired products in moderate to good yields.
Agid:
6047347