Organic Letters · 2018 · 37 citations · 39 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCross-coupling ReactionsHeterocycle SynthesisAmino Acid DerivativesCopper-catalyzed CouplingMild Reaction ConditionsPyrrole ChemistryPyrrole Synthesis
A novel and efficient copper-catalyzed tandem oxidative cyclization/1,2-amino migration of readily available enamino esters for the synthesis of substituted pyrroles has been developed. In this reaction, one C–N bond was cleaved, and two new C–N bonds and one C(sp2)–C(sp2) bond were constructed in one pot. This catalytic system has the obvious advantages of mild reaction conditions and the use of oxygen as the oxidant. The reaction tolerates a wide range of functional groups and is a reliable method for the straightforward synthesis of valuable aminomethyl-substituted pyrroles in good yields.
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Enantiospecific sp2–sp3 coupling of secondary and tertiary boronic esters
Amadeu Bonet, Marcin Odachowski, Daniele Leonori et al. · Nature Chemistry · 2014 · 429 citations · Full text