Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

T Suzuki; M Tokunaga; Y Wakatsuki

doi:10.1021/ol0003937

Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

Org Lett. 2001 Mar 8;3(5):735-7. doi: 10.1021/ol0003937.

Authors

T Suzuki¹, M Tokunaga, Y Wakatsuki

Affiliation

¹ RIKEN (The Institute of Physical and Chemical Research) and PRESTO (Japan Science and Technology Corporation), Wako-shi, Saitama 351-0198, Japan.

PMID: 11259049
DOI: 10.1021/ol0003937

Abstract

[reaction: see text]. Highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphine ligands. Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100 degrees C to give hexanal in 95% yield: 2-hexanone is not detected at all.