Use of lnCl3 as a cocatalyst and a Cl2Pd(DPEphos)-P(2-Furyl)3 catalyst system for one-pot hydrometalation-cross-coupling and carbometalation-cross-coupling tandem processes

被引:57
作者
Qian, MX [1 ]
Huang, ZH [1 ]
Negishi, E [1 ]
机构
[1] Purdue Univ, Hebert C Brown Labs Chem, W Lafayette, IN 47907 USA
关键词
D O I
10.1021/ol049716f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot conversion of alkynes to regio- and stereodefined alkenylmetals containing Al and Zr via hydrometalation or carbometalation followed by their Pd-catalyzed cross-coupling with (E)-ICH=CHBr or (E)-ICH=CHCl proceeds cleanly and selectively to give the corresponding 1-halo-1,3-dienes in excellent yields using a catalyst system consisting Of Cl2Pd(DPEphos), DIBAL-H, and TFP (catalyst A) with InCl3 as a cocatalyst.
引用
收藏
页码:1531 / 1534
页数:4
相关论文
共 45 条
[1]   NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES [J].
BABA, S ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6729-6731
[2]   Enantioselective total synthesis of reveromycin B [J].
Drouet, KE ;
Theodorakis, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :456-457
[3]  
Drouet KE, 2000, CHEM-EUR J, V6, P1987, DOI 10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO
[4]  
2-U
[5]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[6]   Dichlorobis(triphenylphosphine)nickel-catalyzed cross-coupling of aryl chlorides with intramolecularly stabilized group 13 metal alkylating reagents [J].
Gelman, D ;
Schumann, H ;
Blum, J .
TETRAHEDRON LETTERS, 2000, 41 (39) :7555-7558
[7]   Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin [J].
Hu, T ;
Panek, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11368-11378
[8]   Total synthesis of (-)-motuporin [J].
Hu, T ;
Panek, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3000-3001
[9]   Palladium catalyzed cross-methylation of bromoheterocycles with intramolecularly stabilized dimethyl indium reagents [J].
Jaber, N ;
Schumann, H ;
Blum, J .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (04) :565-567
[10]  
Kranenburg M, 1998, EUR J INORG CHEM, P155