Organic Letters · 2013 · 154 citations · 41 references
Natural SciencesChemistryCatalysisComputational ChemistryOrganic ChemistryCoordination ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisBenzothiazole SynthesisCopper-catalyzed CouplingCyclic Ether FormationMild Reaction ConditionsThiazole ChemistryTransition-metal-catalyzed Cross-coupling
Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C-C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.
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