Heteroatom-Directed Aromatic Lithiation: A Versatile Route to the Synthesis of Organochalcogen (Se, Te) Compounds

Chiral and achiral organochalcogen compounds bearing a heteroatom in close proximity are easily accessible via the directed aromatic lithiation route. The lithium chalcogenolates prepared by the insertion of selenium or tellurium into the C-Li bond are used to synthesize various chalcogen compounds such as Se/Te, N donor ligands, dichalcogenides, monomeric metal chalcogenolates, and macrocycles. The differences in the stability and reactivity of the organochalcogen compounds derived from various substrates are described in terms of electronic and stereochemical properties of donor atoms.