N-H activation vs. C-H activation:: ruthenium-catalysed regioselective hydroamination of alkynes and hydroarylation of an alkene with N-methylaniline

被引:144
作者
Uchimaru, Y [1 ]
机构
[1] Natl Inst Mat & Chem Res, Tsukuba, Ibaraki 305, Japan
关键词
D O I
10.1039/a902240f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phenylacetylene and its derivatives undergo regioselective insertion into the N-H bond of N-methylaniline in the presence of Ru-3(CO)(12) catalyst to afford N-methyl-N-(alpha-styryl)anilines in high yields, whereas styrene reacts with the ortho C-H bond of N-methylaniline giving 2-(1-phenylethyl)-N-methylaniline.
引用
收藏
页码:1133 / 1134
页数:2
相关论文
共 19 条
[1]   VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].
BARANGER, AM ;
WALSH, PJ ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763
[2]  
Brunet JJ, 1997, GAZZ CHIM ITAL, V127, P111
[3]   RHODIUM-CATALYZED HYDROAMINATION-HYDROARYLATION OF NORBORNENE WITH ANILINE, TOLUIDINES OR DIPHENYLAMINE [J].
BRUNET, JJ ;
COMMENGES, G ;
NEIBECKER, D ;
PHILIPPOT, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 469 (02) :221-228
[4]   FUNCTIONALIZATION OF ALKENES - CATALYTIC AMINATION OF MONOOLEFINS [J].
BRUNET, JJ ;
NEIBECKER, D ;
NIEDERCORN, F .
JOURNAL OF MOLECULAR CATALYSIS, 1989, 49 (03) :235-259
[5]   RATIONAL DESIGN IN HOMOGENEOUS CATALYSIS - IR(I)-CATALYZED ADDITION OF ANILINE TO NORBORNYLENE VIA N-H ACTIVATION [J].
CASALNUOVO, AL ;
CALABRESE, JC ;
MILSTEIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6738-6744
[6]  
Collmann J. P., 1987, PRINCIPLES APPL ORGA
[7]   The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].
Dorta, R ;
Egli, P ;
Zurcher, F ;
Togni, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858
[8]   Designing new catalytic C-C and C-N bond formations promoted by organoactinides [J].
Eisen, MS ;
Straub, T ;
Haskel, A .
JOURNAL OF ALLOYS AND COMPOUNDS, 1998, 271 :116-122
[9]   STRUCTURE, SYNTHESIS, AND CHEMISTRY OF (PME3)4RU(ETA-2-BENZYNE) - REACTIONS WITH ARENES, ALKENES, AND HETEROATOM-CONTAINING ORGANIC-COMPOUNDS - SYNTHESIS AND STRUCTURE OF A MONOMERIC HYDROXIDE COMPLEX [J].
HARTWIG, JF ;
BERGMAN, RG ;
ANDERSEN, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3404-3418
[10]   Organoactinide-catalyzed intermolecular hydroamination of terminal alkynes [J].
Haskel, A ;
Straub, T ;
Eisen, MS .
ORGANOMETALLICS, 1996, 15 (18) :3773-3775