A practical and benign synthesis of primary amines through ruthenium-catalyzed reduction of nitriles.
The catalytic hydrogenation of nitriles represents an atom-economic and valuable route to amines. In the present study, the ruthenium-catalyzed hydrogenation of various organic nitriles to give primary amines has been examined in detail. Straightforward ruthenium complexes modified by cheap and widely available triphenylphosphine allow for the efficient and general reduction of various aryl, alkyl, and heterocyclic nitriles. By using a practical in situ catalyst composed of [Ru(cod)(methylallyl(2))] and PPh(3), excellent yields and chemoselectivity were achieved. Moreover, the catalyst system displays broad functional group tolerance.
Enthaler
Stephan
S
Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue, Cambridge, MA 02139 , USA.
Junge
Kathrin
K
Addis
Daniele
D
Erre
Giulia
G
Beller
Matthias
M
D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D003365:Costs and Cost Analysis; D055772:Green Chemistry Technology / Q000191:economics / Q000379:methods*; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry; D011312:Pressure; D012428:Ruthenium / Q000737:chemistry*; D013696:Temperature
D000588:Amines; D009570:Nitriles; D010720:Phosphines; D012428:Ruthenium; C044646:phosphine