4.5 Article

Ligand-Free Pd-Catalyzed Reductive Mizoroki-Heck Reaction Strategy for the One-Pot Synthesis of Functionalized Oxygen Heterocycles in Deep Eutectic Solvents

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 26, Issue 3, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200814

Keywords

Deep eutectic solvents; Mizoroki-Heck reaction; Oxygen heterocycles; Tetrahydrofurans; Tetrahydropyrans

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Deep eutectic solvent, choline chloride/glycerol, has been proven to be an effective and sustainable reaction medium for the synthesis of valuable tetrahydrofuran and tetrahydropyran derivatives. The reaction proceeds under aerobic conditions, without the need for additional ligands, and has a good substrate scope.
A Deep Eutectic Solvent, choline chloride/glycerol (1 : 2 mol mol(-1)), proved to be an effective and sustainable reaction medium to promote telescoped, one-pot Mizoroki-Heck cross-coupling/reduction processes between 2,3-dihydrofuran or 3,4-dihydro-2H-pyran and several (hetero)aryl halides to easily access valuable 2-(hetero)aryl tetrahydrofuran (THF) or tetrahydropyran derivatives in up to 95 % yield. Notably, the whole transformation takes place under aerobic conditions, in the absence of additional ligands, and with a good substrate scope. The practicability of the method is also exemplified by the sustainable synthesis of two key THF derivatives, which are side chains of pharmacologically relevant inhibitors of Kv1.2 channel.

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