Angewandte Chemie International Edition · 2020 · 97 citations · 71 references
Natural SciencesChemistryCatalysisDrug DiscoverySynthetic Medicinal ChemistryAmino Acid ChemistryCatalytic MechanismsCross-coupling ReactionsPhotocatalysisPhotochemistryRadical ReactionsAmino Acid DerivativesElectron TransferFunctional Group ToleranceNickel CatalysisPhotocatalytic SynthesisPhotoredox CatalysisPhotoredox Cross-couplingPhotoredox Functionalization
A highly chemo- and regioselective intermolecular 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.
71
Photoredox Catalysis in Organic Chemistry
Megan H. Shaw, Jack Twilton, David W. C. MacMillan · The Journal of Organic Chemistry · 2016 · 3.1K citations · Full text
Zhiwei Zuo, Derek T. Ahneman, Lingling Chu et al. · Science · 2014 · 1.6K citations · Full text
A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents
Tian Qin, Josep Cornellà, Chao Li et al. · Science · 2016 · 744 citations
John C. Tellis, Christopher B. Kelly, David N. Primer et al. · Accounts of Chemical Research · 2016 · 687 citations · Full text