A Practical and Benign Synthesis of Primary Amines through Ruthenium-Catalyzed Reduction of Nitriles

被引:98
作者
Enthaler, Stephan [1 ]
Junge, Kathrin [2 ]
Addis, Daniele [2 ]
Erre, Giulia [3 ]
Beller, Matthias [2 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[3] Rhein Westfal TH Aachen, ITMC, CAT Catalyt Ctr, D-52074 Aachen, Germany
关键词
amines; homogeneous catalysis; hydrogenation; nitriles; ruthenium;
D O I
10.1002/cssc.200800185
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 PPh3, excellent yields and chemoselectivity were achieved. Moreover, the catalyst system displays broad functional group tolerance.
引用
收藏
页码:1006 / 1010
页数:5
相关论文
共 58 条
[1]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[2]   Origins, current status, and future challenges of green chemistry [J].
Anastas, PT ;
Kirchhoff, MM .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694
[3]   Catalysis as a foundational pillar of green chemistry [J].
Anastas, PT ;
Kirchhoff, MM ;
Williamson, TC .
APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :3-13
[4]  
[Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22
[5]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[6]   Base-catalyzed amination of olefins: an example of an environmentally friendly synthesis of amines [J].
Beller, M ;
Breindl, C .
CHEMOSPHERE, 2001, 43 (01) :21-26
[7]   Preparation, characterization, and performance of the supported hydrogen-bonded ruthenium catalyst [(sulphos)Ru(NCMe)3](OSO2CF3)/SiO2.: Comparisons with analogous homogeneous and aqueous-biphase catalytic systems in the hydrogenation of benzylideneacetone and benzonitrile [J].
Bianchini, C ;
Dal Santo, V ;
Meli, A ;
Oberhauser, W ;
Psaro, R ;
Vizza, F .
ORGANOMETALLICS, 2000, 19 (13) :2433-2444
[8]   Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].
Buchwald, SL ;
Mauger, C ;
Mignani, G ;
Scholz, U .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39
[9]  
Chin C.S., 1992, CATAL LETT, V14, P135, DOI DOI 10.1007/BF00764228
[10]   Hydrogenation of aldehydes, esters, imines, and ketones catalyzed by a ruthenium complex of a chiral tridentate ligand [J].
Clarke, Matthew L. ;
Diaz-Valenzuela, M. Belen ;
Slawin, Alexandra M. Z. .
ORGANOMETALLICS, 2007, 26 (01) :16-19