Angewandte Chemie · 2017 · 107 citations · 76 references
Natural SciencesChemical EngineeringChemistryBiocatalysisCatalysisOrganometallic ChemistryAmino Acid ChemistryHeterocycle SynthesisPeptide Bond ChemistryPeptide ChemistryAmino AcidsCatalytic Cycle AnalysisCatalytic Cycle MechanismsCyclic PeptidesFluorescent LabelsManganese CatalysisMolecular Self-assemblySubstrate Scope
Abstract Manganese(I)‐catalyzed C−H alkynylations with organic halides occurred with unparalleled substrate scope, and thus enabled step‐economical C−H functionalizations with silyl, aryl, alkenyl, and alkyl haloalkynes. The versatility of the manganese(I) catalysis manifold enabled C−H couplings with haloalkynes featuring, among others, fluorescent labels, steroids, and amino acids, thereby setting the stage for peptide ligation as well as the efficient molecular assembly of acyclic and cyclic peptides. A plausible catalytic cycle was proposed.
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Christian W. Tornøe, Caspar Christensen, Morten Meldal · The Journal of Organic Chemistry · 2002 · 8.5K citations