A Fortuitous, Mild Catalytic Carbon–Carbon Bond Hydrogenolysis by a Phosphine-Free Catalyst
Loorthuraja Rasu A , Ben Rennie A , Mark Miskolzie A and Steven H. Bergens A BA Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada.
B Corresponding author. Email: sbergens@ualberta.ca
Australian Journal of Chemistry 69(5) 561-564 https://doi.org/10.1071/CH15792
Submitted: 17 December 2015 Accepted: 3 March 2016 Published: 6 April 2016
Abstract
The putative catalyst trans-[Ru((S,S)-skewphos)(H)2((R,R)-dpen)] (skewphos = 2,4-bis(diphenylphosphino)pentane; dpen = 1,2-diphenylethylenediamine) transforms the trifluoroacetyl amide 2,2,2-trifluoro-1-(piperidin-1-yl)ethanone under mild conditions (4 atm H2, room temperature, 4–24 h, 1 mol-% Ru, 15 mol-% KOtBu in tetrahydrofuran) to generate the formylated amine 1-formylpiperidine and fluoroform via C–C bond hydrogenolysis. Catalysts are also prepared by reacting cis-[Ru(η3-C3H5)(MeCN)2(COD)]BF4 (COD = 1,5-cyclooctadiene) with diamine ligands in situ. Low-temperature NMR studies provided insight into this reaction.
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