A highly diastereoselective and straightforward synthesis for (Z)-2-fluoroallylic alcohols via a Nozaki-Hiyama-Kishi-type reaction with the corresponding bromofluoroolefins was developed, providing an easy access to highly interesting fluorinated synthons.
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A General Three-Component Nozaki-Hiyama-Kishi-Type Reaction Enabled by Delayed Radical-Polar Crossover.
J Am Chem Soc
January 2025
Organisch-Chemisches Institut, Universität Münster, Münster 48149, Germany.
Nozaki-Hiyama-Kishi (NHK) reactions offer a mild approach for the formation of alcohol motifs through radical-polar crossover-based pathways from various radical precursors. However, the application of multicomponent NHK-type reactions, which allow the formation of multiple bonds in a single step, has been largely restricted to bulky alkyl radical precursors, thus limiting their expanded utilization. Herein, we disclose a general three-component NHK-type reaction enabled by delayed radical-polar crossover, which efficiently tolerates a plethora of radical precursors that were previously unavailable.
View Article and Find Full Text PDFA novel diastereoselective synthesis of (Z)-fluoroalkenes via a Nozaki-Hiyama-Kishi-type reaction.
J Org Chem
March 2005
INSA de ROUEN, IRCOF, UMR CNRS6014, 1 rue Tesnière, 76131 Mont Saint-Aignan, France.
A highly diastereoselective and straightforward synthesis for (Z)-2-fluoroallylic alcohols via a Nozaki-Hiyama-Kishi-type reaction with the corresponding bromofluoroolefins was developed, providing an easy access to highly interesting fluorinated synthons.
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