Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 23, Pages 5412-5420Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901040
Keywords
manganese; alkyl complexes; hydrogenation; nitriles; migratory insertion
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Funding
- Austrian Science Fund (FWF) [P29584-N28]
- Fundacao para a Ciencia e Tecnologia [UID/QUI/00100/2013]
- Austrian Science Fund (FWF) [P29584] Funding Source: Austrian Science Fund (FWF)
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An efficient additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)(3)(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively unsaturated Mn(I) hydride catalyst [Mn(dpre)(CO)(2)(H)]. A range of aromatic and aliphatic nitriles were efficiently and selectively converted into primary amines in good to excellent yields. The hydrogenation of nitriles proceeds at 100 degrees C with a catalyst loading of 2 mol % and a hydrogen pressure of 50 bar. Mechanistic insights are provided by means of DFT calculations.
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