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Ag II ‐Mediated Synthesis of β‐Fluoroketones by Oxidative Cyclopropanol Opening
Author(s) -
Deng Yuanlin,
Kauser Nabeelah I.,
Islam Shahidul M.,
Mohr Justin T.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700899
Subject(s) - chemistry , regioselectivity , fluorine , homolysis , bond cleavage , ring (chemistry) , selectivity , oxidative cleavage , cleavage (geology) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , radical , geotechnical engineering , fracture (geology) , engineering
A regioselective synthesis of β‐fluorinated ketones by silver(II)‐mediated ring opening is described. Commercially available AgF 2 serves as both an oxidant and fluorine‐atom source. A variety of β‐fluorinated ketones are efficiently prepared from tertiary cyclopropanol precursors, offering a straightforward approach for the introduction of a fluorine atom at a remote site. Selectivity is observed in the site of bond cleavage, which leads to fluorination at the more substituted site. A radical mediated sequential homolytic C–C bond cleavage and C–F bond formation is suggested.