S. Sakaki, T. Kojima, T. Arai
1994
Citations
0
Influential Citations
5
Citations
Journal
Journal of The Chemical Society-dalton Transactions
Abstract
Chloro(5,10,15,20-tetraphenylporphyrinato)iron(III) in tetrahydrofuran-methanol catalysed the hydrogenation of α,β-unsaturated esters by NaBH4 to the saturated esters; turnovers of up to 4580 h–1 have been attained for the hydrogenation of ethyl 2-methylbut-2-enoate. Deuterium labelling studies showed that the H– of NaBH4 and the H+ of MeOH add to the β- and α-carbons of the double bond. A slower hydrogenation of oct-1-ene was accompanied by isomerization to oct-2-enes. Spectroscopy (UV/VIS, 1H NMR and ESR) suggests that hydrogenation proceeds via an iron(II) intermediate, and an alkyl-iron(II) species seems likely.