Visible-light-initiated difluoromethylation of arene diazonium tetrafluoroborates

A mild and efficient method for the radical addition of -aryl-,-difluoroenol silyl with arene diazonium tetrafluoroborates at room temperature has been disclosed, which involves an innate radical long chain cycle, so only a small amount (0.05 mol%) of photocatalyst and a short light exposure time ar...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2016-05, Vol.52 (35), p.5965-5968
Hauptverfasser: Wu, Ye-bin, Lu, Guo-ping, Zhou, Bao-jing, Bu, Mei-jie, Wan, Li, Cai, Chun
Format: Artikel
Sprache:eng
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Zusammenfassung:A mild and efficient method for the radical addition of -aryl-,-difluoroenol silyl with arene diazonium tetrafluoroborates at room temperature has been disclosed, which involves an innate radical long chain cycle, so only a small amount (0.05 mol%) of photocatalyst and a short light exposure time are required as radical initiators. A proposed mechanism for the transformation is also illustrated based on the results of control experiments and quantum calculations. A variety of -aryl-,-difluoroketones were formed in moderate to high yields, and can be easily further transformed into various difluoromethylarenes under basic conditions. A mild and efficient method for the radical addition of -aryl-,-difluoroenol silyl with arene diazonium tetrafluoroborates at room temperature has been disclosed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc00177g