Ligands for palladium-catalyzed cross-couplings of alkyl halides: Use of an alkyldiaminophosphane expands the scope of the Stille reaction

被引:78
作者
Tang, HF [1 ]
Menzel, K [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
cross-coupling; homogeneous catalysis; palladium; phosphane ligands; Stille reaction;
D O I
10.1002/anie.200352668
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkyldiaminophosphanes (PR(NR′2)2) are a new class of ligands for palladium-catalyzed cross-couplings of alkyl halides (see scheme). In comparison with trialkylphosphanes, alkyldiaminophosphanes furnish more versatile catalysts for Stille reactions of alkyl bromides and achieve efficient couplings with both vinyl and aryl stannanes, Furthermore, Pd/PR(NR′2)2 provides the first method for accomplishing Stille cross-couplings of simple alkyl iodides that bear β-hydrogen atoms.
引用
收藏
页码:5079 / 5082
页数:4
相关论文
共 40 条
[1]  
[Anonymous], ANGEW CHEM
[2]  
Cardenas D. J., 1999, ANGEW CHEM, V111, P3201
[3]   Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].
Cárdenas, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387
[4]  
Cárdenas DJ, 1999, ANGEW CHEM INT EDIT, V38, P3018, DOI 10.1002/(SICI)1521-3773(19991018)38:20<3018::AID-ANIE3018>3.0.CO
[5]  
2-F
[6]   Highly electron rich alkyl- and dialkyl-N-pyrrolidinyl phosphines: an evaluation of their electronic and structural properties [J].
Clarke, ML ;
Holliday, GL ;
Slawin, AMZ ;
Woollins, JD .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (06) :1093-1103
[7]   P-N bond formation as a route to highly electron rich phosphine ligands [J].
Clarke, ML ;
Cole-Hamilton, DJ ;
Slawin, AMZ ;
Woollins, JD .
CHEMICAL COMMUNICATIONS, 2000, (20) :2065-2066
[8]  
Devasagayaraj A, 1995, ANGEW CHEM INT EDIT, V34, P2723
[9]  
DEVASAGAYARAJ A, 1995, ANGEW CHEM, V107, P2952
[10]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222