1,4-Butanediol as a reducing agent in transfer hydrogenation reactions.
1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions.
Maytum
Hannah C
HC
Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
Francos
Javier
J
Whatrup
David J
DJ
Williams
Jonathan M J
JM
D000475:Alkenes / Q000737:chemistry; D002072:Butylene Glycols / Q000737:chemistry*; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D019163:Reducing Agents / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D002072:Butylene Glycols; D007097:Imines; D007783:Lactones; D020005:Propanols; D019163:Reducing Agents; C006463:allyl alcohol; D012428:Ruthenium; C039681:1,4-butanediol