Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

摘要: Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 both stoichiometric catalytic copper-mediated reactions, also examples nickel-mediated under modified Chan–Lam cross-coupling conditions using various nucleophiles; include chemo- regioselective N-arylations or O-arylations. The utilization nucleophiles as coupling partners together with reaction optimization (including choice copper source, ligands, base, other additives), limitations, scope, mechanisms are examined; these benefitted development efficient milder methods. synthesis medicinally valuable pharmaceutically important nitrogen heterocycles, including isotope-labeled compounds, is included. can now form twelve different C–element bonds, making it one most diverse mild known chemistry. 1 Introduction 2 Construction C–N C–O Bonds 2.1 C–N Bond Formation 2.1.1 Original Discovery via Stoichiometric Copper-Mediated 2.1.2 Copper-Catalyzed 2.1.3 Coupling Azides, Sulfoximines, Sulfonediimines Nitrogen­ Nucleophiles 2.1.4 N,N-Dialkylhydroxylamines 2.1.5 Enolate Coupling sp3-Carbon 2.1.6 Nickel-Catalyzed 2.1.7 Amino Acids 2.1.8 Alkylboron Reagents 2.1.9 Electron-Deficient Heteroarylamines 2.1.10 Selective Synthesis Heterocycle-Containing Compounds 2.1.11 Using Sulfonato-imino Copper(II) Complexes 2.2 C–O 2.2.1 (Hetero)arylboron 2.2.2 Alkyl- Alkenylboron 3 C–Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Forma tion Modified Conditions 4 Conclusions