Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

Abstract

A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence of wet trifluoroacetic acid, in addition to phosphinoylisocoumarins, phosphorus-free isocoumarins were also obtained. Key products were characterized by single crystal X-ray crystallography.

Keywords

• allenes
• indoles
• isocoumarins
• organophosphorus
• phosphinoyl-heterocycles
• propargyl alcohols