A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe3)2

Abstract

A chemo- and regioselective synthesis of 2-benzhydryl and 2,3-disubstituted indoles via cyclization and regiocontrolled Truce–Smiles (T–S) rearrangement is disclosed. A cascade 5-endo-dig cyclization of 2-amino diphenylacetylenes mediated by KN(SiMe₃)₂ is followed by a regiocontrolled T–S reaction. This system provides the first example of T–S regioselectivity and is controlled by ligands on K⁺.