Synthesis and Properties of Phosphoroselenoic Acids and Their salts Bearing Binaphthyl Groups

Abstract

Phosphoroselenoyl chlorides were prepared by reacting four types of substituted 1,1′-bi-2-naphthols, PCl₃, and elemental selenium in the presence of Et₃N. The chlorides were converted to the corresponding acids via acid ammonium salts with high efficiency. The spectroscopic properties of these derivatives were used to elucidate the structures of the acids. Finally, the acids were applied to the hydrogenation reaction of imines using Hantzsch ester as a hydrogen donor.

Keywords:

• Binaphthyl groups
• organocatalysts
• phosphoroselenoic acid salts
• phosphoroselenoyl chlorides

Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday. This work was supported in part by Grant-in-Aid for Scientific Research on Priority Areas (No. 20036020 ‘‘Synergy of Elements,’’ and Nos. 19020020 and 19020062 ‘‘Advanced Molecular Transformations of Carbon Resources’’) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.