Organic Letters · 2019 · 64 citations · 35 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisOrganic SynthesisAlkyne Cycloaddition ReactionsBuilding Block MethodologyFunctional Group ToleranceHeterocycle FunctionalizationMild Reaction ConditionsPyrazole ChemistryPyrazole SynthesisSubstrate Scope
A silver-mediated [3 + 2] cycloaddition of "CNN" and "C≡C" for constructing pyrazoles has been described. The "CNN" building block used is N-isocyanoiminotriphenylphosphorane, which is a stable, safe, easy-to-handle, and odorless solid isocyanide. The reaction is characterized by its mild conditions, broad substrate scope, and excellent functional group tolerance.
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Shin Kamijo, Chikashi Kanazawa, Yoshinori Yamamoto · Journal of the American Chemical Society · 2005 · 314 citations