The First Anti-Markovnikov Hydration of Terminal Alkynes: Formation of Aldehydes Catalyzed by a Ruthenium(II)/Phosphane Mixture

Makoto Tokunaga; Yasuo Wakatsuki

doi:10.1002/(SICI)1521-3773(19981102)37:20<2867::AID-ANIE2867>3.0.CO;2-E

The First Anti-Markovnikov Hydration of Terminal Alkynes: Formation of Aldehydes Catalyzed by a Ruthenium(II)/Phosphane Mixture

Angew Chem Int Ed Engl. 1998 Nov 2;37(20):2867-2869. doi: 10.1002/(SICI)1521-3773(19981102)37:20<2867::AID-ANIE2867>3.0.CO;2-E.

Authors

Makoto Tokunaga¹, Yasuo Wakatsuki¹

Affiliation

¹ The Institute of Physical and Chemical Research (RIKEN), Wako-shi, Saitama, 351-0198 (Japan), Fax: (+81) 48-462-4665.

Abstract

With the right auxiliary phosphane ligands-for example, pentafluorophenyldiphenylphosphane or the sodium salt of 3,3',3″-phosphinidynetris(benzenesulfonic acid)-the ruthenium(II)-catalyzed hydration of terminal alkynes to aldehydes proceeds by the previously unknown anti-Markovnikov addition of water [Eq. (a)]. Complexes of the type [RuCl₂ (PR₂ R₂^' R″)_x ] (R=alkyl, Ph) are discussed as catalytically active species.

Keywords: Aldehydes; Alkynes; Homogeneous catalysis; Hydration; Ruthenium.