Synthesis of lanthanide(II)-imine complexes and their use in carbon-carbon and carbon-nitrogen unsaturated bond transformation

被引:63
作者
Takaki, K [1 ]
Komeyama, K [1 ]
Takehira, K [1 ]
机构
[1] Hiroshima Univ, Grad Sch Engn, Dept Chem & Chem Engn, Higashihiroshima 7398527, Japan
关键词
azalanthanacyclopropane; lanthanide catalyst; hydrosilylation; dehydrogenative silylation; hydrophosphination;
D O I
10.1016/j.tet.2003.06.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ytterbium and samarium metals reduced aromatic ketimines to give directly divalent azalanthanacyclopropane complexes 1 quantitatively, the structure of which was characterized by X-ray analysis. The imine complexes 1 catalyzed dehydrogenative silylation of terminal alkynes, hydrosilylation of imines and alkenes, and intermolecular hydrophosphination of alkynes. Moreover, dehydrogenative double silylation of conjugated dienes was achieved with 1. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10381 / 10395
页数:15
相关论文
共 52 条
[1]  
[Anonymous], COMPREHENSIVE ORGANO
[2]   Intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes catalyzed by organolanthanides: Scope, selectivity, and mechanism [J].
Douglass, MR ;
Stern, CL ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10221-10238
[3]   INVESTIGATION OF ORGANOLANTHANIDE-BASED CARBON-CARBON BOND FORMATION - SYNTHESIS, STRUCTURE, AND COUPLING REACTIVITY OF ORGANOLANTHANIDE ALKYNIDE COMPLEXES, INCLUDING THE UNUSUAL STRUCTURES OF THE TRIENEDIYL COMPLEX [(C5ME5)2SM]2[MU-ETA(2)-ETA(2)-PH(CH2)2C=C=C=C-(CH2)2PH] AND THE UNSOLVATED ALKYNIDE [(C5ME5)2SM(CCCME3)]2 [J].
EVANS, WJ ;
KEYER, RA ;
ZILLER, JW .
ORGANOMETALLICS, 1993, 12 (07) :2618-2633
[4]   ALKYNE COUPLING REACTIONS MEDIATED BY ORGANOLANTHANIDES - PROBING THE MECHANISM BY METAL AND ALKYNE VARIATION [J].
FORSYTH, CM ;
NOLAN, SP ;
STERN, CL ;
MARKS, TJ ;
RHEINGOLD, AL .
ORGANOMETALLICS, 1993, 12 (09) :3618-3623
[5]   ORGANOLANTHANIDE-CATALYZED DEHYDROGENATIVE COUPLING OF SILANES - MECHANISTIC IMPLICATIONS [J].
FORSYTH, CM ;
NOLAN, SP ;
MARKS, TJ .
ORGANOMETALLICS, 1991, 10 (08) :2543-2545
[6]   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
[7]   NEW SYNTHETIC REACTIONS BY MEANS OF RARE-EARTH REAGENTS [J].
FUJIWARA, Y ;
TAKAKI, K ;
TANIGUCHI, Y .
JOURNAL OF ALLOYS AND COMPOUNDS, 1993, 192 (1-2) :200-204
[8]   Oxidative addition of HP(O)Ph(2) to platinum(0) and palladium(0) complexes and palladium-catalyzed regio- and stereoselective hydrophosphinylation of alkynes [J].
Han, LB ;
Choi, N ;
Tanaka, M .
ORGANOMETALLICS, 1996, 15 (15) :3259-3261
[9]   Palladium-catalyzed hydrophosphorylation of alkynes via oxidative addition of HP(O)(OR)(2) [J].
Han, LB ;
Tanaka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1571-1572
[10]   REVERSIBLE CARBON-CARBON BOND FORMATION IN ORGANOLANTHANIDE SYSTEMS - PREPARATION AND PROPERTIES OF LANTHANIDE ACETYLIDES [CP-ASTERISK-2LNCCR]N AND THEIR REARRANGEMENT PRODUCTS [CP-ASTERISK-2LN]2(MU-ETA(2)-ETA(2)-RC4R) (LN = LA, CE, R = ALKYL) [J].
HEERES, HJ ;
NIJHOFF, J ;
TEUBEN, JH ;
ROGERS, RD .
ORGANOMETALLICS, 1993, 12 (07) :2609-2617