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Insight into catalyst speciation and hydrogen co-evolution during enantioselective formic acid-driven transfer hydrogenation with bifunctional ruthenium complexes from multi-technique operando reaction monitoring†
Faraday Discussions ( IF 3.712 ) Pub Date : 2019-06-11 , DOI: 10.1039/c9fd00060g
Daniel B. G. Berry, Anna Codina, Ian Clegg, Catherine L. Lyall, John P. Lowe, Ulrich Hintermair

Transfer hydrogenation of acetophenone from formic acid/triethylamine mixtures catalysed by the Ikariya–Noyori complex [(mesitylene)RuCl(R,R)-(TsDPEN)] has been investigated using simultaneous high-resolution FlowNMR and FlowUV-Vis spectroscopies coupled with on-line sampling head-space mass spectrometry and chiral high-performance liquid chromatography using an integrated, fully automated recirculating flow setup. In line with previous observations, the combined results show a gradual switch from formic acid dehydrogenation to hydrogen transfer mediated by the same Ru-hydride complex, and point to a Ru-formate species as the major catalyst intermediate. Hydrogen bonding in the formic acid/triethylamine mixture emerges as a sensitive 1H NMR probe for the transfer hydrogenation activity of the system and can be used to locate optimum reaction conditions.
更新日期:2019-12-04

 

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