An electrochemically intramolecular functionalization of C(sp)-H bonds with masked oxygen nucleophiles was developed. With KI as the catalyst and electrolyte, diverse trisubstituted 2-oxazolines were constructed in good to excellent yields. This newly developed electrochemical dehydrogenative approach features external oxidant-free and additive-free conditions.
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Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones.
Org Lett
May 2018
Engineering Technology Research Center of Henan Province for Solar Catalysis, College of Chemistry and Pharmaceutical Engineering , Nanyang Normal University, Nanyang , Henan 473061 , P. R. China.
An electrochemically intramolecular functionalization of C(sp)-H bonds with masked oxygen nucleophiles was developed. With KI as the catalyst and electrolyte, diverse trisubstituted 2-oxazolines were constructed in good to excellent yields. This newly developed electrochemical dehydrogenative approach features external oxidant-free and additive-free conditions.
View Article and Find Full Text PDFA straightforward, one-pot protocol for the preparation of libraries of 2-oxazolines.
J Comb Chem
November 2005
Serono Pharmaceutical Research Institute, 14 Chemin des Aulx, 1228 Plan-les-Ouates, Geneva, Switzerland.
A practical protocol for the parallel synthesis of 2-oxazolines using polymer-supported reagents is described. Polymer-supported Mukaiyama reagent is used to couple a carboxylic acid with an amino alcohol, giving a beta-hydroxyamide, which is then cyclized in situ using either polymer-supported sulfonyl chloride resin or polymer-bound 2-fluoropyridinium triflate. Both 2,4-disubstituted and 2,4,5-trisubstituted 2-oxazolines are obtained in high yields and excellent purities after a simple resin filtration and solvent evaporation routine.
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