The hydration of terminal alkynes and of propargylic alcohols to the corresponding aldehyde derivatives is conveniently carried out at 60 °C in an aqueous micellar environment, in the presence of 5 mol% of the indenyl ruthenium(II) complex [Ru(h5-C9H7)Cl(Pph3)2]. Higher yelds and improved regioselectivity of aldehyde versus ketone as well as reaction conditions, in particular temperature and catalyst load, are found with respect to a solvent mixture 2-propanol-water, due to the aggregating conditions of the micellar solution. The reactions of the propargylic alcohols indicate the tolarance of the hydroxy functionality by the ruthenium complex.
Hydration of terminal alkynes to aldehydes in aqueous micellar solutions by ruthenium(II) catalysis; first anti-Markovnikov addition of water to propargylic alcohols
Bassetti Mauro;Mancini Giovanna
2001
Abstract
The hydration of terminal alkynes and of propargylic alcohols to the corresponding aldehyde derivatives is conveniently carried out at 60 °C in an aqueous micellar environment, in the presence of 5 mol% of the indenyl ruthenium(II) complex [Ru(h5-C9H7)Cl(Pph3)2]. Higher yelds and improved regioselectivity of aldehyde versus ketone as well as reaction conditions, in particular temperature and catalyst load, are found with respect to a solvent mixture 2-propanol-water, due to the aggregating conditions of the micellar solution. The reactions of the propargylic alcohols indicate the tolarance of the hydroxy functionality by the ruthenium complex.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
