Dehydrogenative silylation of amines and hydrosilylation of imines catalyzed by ytterbium-imine complexes

被引:59
作者
Takaki, K [1 ]
Kamata, T [1 ]
Miura, Y [1 ]
Shishido, T [1 ]
Takehira, K [1 ]
机构
[1] Hiroshima Univ, Fac Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan
关键词
D O I
10.1021/jo982154r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dehydrogenative silylation of primary and secondary amines with triphenylsilane was catalyzed by ytterbium-imine complexes, [Yb(eta(2)-Ph2CNAr)(hmpa)(n)], to give aminosilanes in good yields. In the reaction with diphenyl- and phenylsilanes, diaminosilanes were formed as major products. Whereas n- and sec-alkylamines were readily silylated, tert-alkylamines and aromatic amines exhibited lower reactivities. Moreover, hydrosilylation of imines has been achieved by using phenylsilane and the imine complexes (Ar = Ph, C6H4F-4), giving rise to mono- and diaminosilanes. The two reactions were in agreement as regards the product selectivities and yields.
引用
收藏
页码:3891 / 3895
页数:5
相关论文
共 21 条
[1]   CHIRAL ORGANOLANTHANIDE COMPLEXES FOR ENANTIOSELECTIVE OLEFIN HYDROGENATION [J].
CONTICELLO, VP ;
BRARD, L ;
GIARDELLO, MA ;
TSUJI, Y ;
SABAT, M ;
STERN, CL ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2761-2762
[2]  
Edelmann F. T., 1996, TOP CURR CHEM, V179, P247
[3]   ORGANOLANTHANIDE-CATALYZED DEHYDROGENATIVE COUPLING OF SILANES - MECHANISTIC IMPLICATIONS [J].
FORSYTH, CM ;
NOLAN, SP ;
MARKS, TJ .
ORGANOMETALLICS, 1991, 10 (08) :2543-2545
[4]   REGIOSELECTION AND ENANTIOSELECTION IN ORGANOLANTHANIDE-CATALYZED OLEFIN HYDROSILYLATION - A KINETIC AND MECHANISTIC STUDY [J].
FU, PF ;
BRARD, L ;
LI, YW ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7157-7168
[5]   CHIRAL ORGANOLANTHANIDES DESIGNED FOR ASYMMETRIC CATALYSIS - A KINETIC AND MECHANISTIC STUDY OF ENANTIOSELECTIVE OLEFIN HYDROAMINATION/CYCLIZATION AND HYDROGENATION BY C-1-SYMMETRICAL ME(2)SI(ME(4)C(5))(C(5)H(3)R-ASTERISK)LN COMPLEXES WHERE R-ASTERISK=CHIRAL AUXILIARY [J].
GIARDELLO, MA ;
CONTICELLO, VP ;
BRARD, L ;
GAGNE, MR ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10241-10254
[6]   Coordinative unsaturation in chiral organolanthanides. Synthetic and asymmetric catalytic mechanistic study of organoyttrium and -lutetium complexes having pseudo-meso Me(2)Si(eta(5)-RC(5)H(3))(eta(5)-R(*)C(5)H(3)) ancillary ligation [J].
Haar, CM ;
Stern, CL ;
Marks, TJ .
ORGANOMETALLICS, 1996, 15 (07) :1765-1784
[7]  
Imamoto T., 1994, LANTHANIDES ORGANIC
[8]   HIGHLY REACTIVE ORGANOLANTHANIDES - A MECHANISTIC STUDY OF CATALYTIC OLEFIN HYDROGENATION BY BIS(PENTAMETHYLCYCLOPENTADIENYL) AND RELATED 4F COMPLEXES [J].
JESKE, G ;
LAUKE, H ;
MAUERMANN, H ;
SCHUMANN, H ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8111-8118
[9]   LANTHANIDES IN ORGANIC-SYNTHESIS [J].
KAGAN, HB ;
NAMY, JL .
TETRAHEDRON, 1986, 42 (24) :6573-6614
[10]   The chemistry of the triethylsilicyl group [J].
Kraus, CA ;
Nelson, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :195-202