Synthesis of aldehydes by hydration of alkynes
Complexes derived from air-stable [CpRu(6-naphthalene)]PF6 and 6-aryl-2-diphenylphosphinopyridines efficiently catalyze the anti-Markovnikov hydration of terminal alkynes to give aldehydes.
A. Labonne, T. Kribber, L. Hintermann, Org. Lett., 2006, 8, 5853-5856.
A highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes provides n-aldehydes in the presence of a catalytic amount of RuCpCl(dppm).
T. Sukuzi, M. Tokunaga, Y. Wakatsuki, Org. Lett., 2001, 3, 119-122.
A ruthenium catalyst was identified, which allows highly regioselective anti-Markovnikov hydration of terminal alkynes compatible with a wide range of functional groups.
F. Chevallier, B. Breit, Angew. Chem. Int. Ed., 2006, 45, 1599-1602.
Stereodefined enol derivatives of aldehydes are prepared from terminal alkynes through Cp2ZrCl2-catalyzed methylalumination and subsequent oxygenation with peroxyzinc species and electrophilic trapping with carboxylic anydrides. The tandem carbometalation/oxygenation tolerates free and protected alcohols, heterocycles, olefins, and nitriles.
J. R. DeBergh, K. M. Spivey, J. M. Ready, J. Am. Chem. Soc., 2008, 130, 7828-7829.