Catalytic Amination of ß-(Hetero)arylethyl Ethers by Phosphazene Base t-Bu-P4.

ABSTRACT

We describe the catalytic amination of ß-(hetero)arylethyl ethers with amines using the organic superbase t-Bu-P4 to obtain ß-(hetero)arylethylamines. The reaction has a broad substrate scope and allows the transformations of electron-deficient and electron-neutral ß-(hetero)arylethyl ethers with various amines including pyrrole, N-alkylaniline, diphenylamine, aniline, indole, and indoline derivatives. Mechanistic studies indicate a two-reaction pathway of MeOH elimination from the substrate to form a (hetero)arylalkene followed by the hydroamination of the alkene.