Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging suzuki coupling reactions

被引:132
作者
Colacot, TJ
Shea, HA
机构
[1] Johnson Matthey, Catalysis & Chiral Technol, W Deptford, NJ 08066 USA
[2] Pharm Eco, Catalyt Serv, Devens, MA 01434 USA
关键词
D O I
10.1021/ol048598t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use Of CP2Fe(PR2)(2)PdCl2 (R = i-Pr and t-Bu) in Suzuki coupling reactions were illustrated using a high throughput screening approach. The di-tbpfPdCl(2) catalyst was shown to be the more active catalyst for unactivated and sterically challenging aryl chlorides. Comparison studies using the commercial catalysts dppfPdCl(2), (Ph3P)(2)PdCl2, (Cy3P)(2)PdCl2, DPEPhosPdCl(2), dppbPdCl(2), dppePdCl(2), Pd(t-BU3P)(2), and [Pd-(mu-Br)(t-Bu3P)](2) were also done for selected cases to demonstrate the superior activities of di-tbpfPdCl(2) and di-isoppfPdCl(2).
引用
收藏
页码:3731 / 3734
页数:4
相关论文
共 48 条
[1]   Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex [J].
Bei, XH ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6797-6803
[2]   N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction [J].
Böhm, VPW ;
Gstöttmayr, CWK ;
Weskamp, T ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190
[3]  
BOYLES AL, 1998, TETRAHEDRON LETT, V39, P7766
[4]   1,1'-BIS[(ALKYL/ARYL)PHOSPHINO]FERROCENES - SYNTHESIS AND METAL-COMPLEX FORMATION - CRYSTAL-STRUCTURE OF 3 METAL-COMPLEXES OF FE(ETA-5-C5H4PPH2)2- [J].
BUTLER, IR ;
CULLEN, WR ;
KIM, TJ ;
RETTIG, SJ ;
TROTTER, J .
ORGANOMETALLICS, 1985, 4 (06) :972-980
[5]  
Colacot TJ, 2001, PLATIN MET REV, V45, P22
[6]   Synthesis, single crystal X-ray structure determination and NMR studies of Cp2Fe(PPh2)2PtPh2 and Cp2Fe(PPh2)2PtI2 [J].
Colacot, TJ ;
Teichman, RA ;
Cea-Olivares, R ;
Alvarado-Rodriguez, JG ;
Toscano, RA ;
Boyko, WJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 557 (02) :169-179
[7]   High-throughput screening studies of fiber-supported catalysts leading to room-temperature Suzuki coupling [J].
Colacot, TJ ;
Gore, ES ;
Kuber, A .
ORGANOMETALLICS, 2002, 21 (16) :3301-3304
[8]   Synthesis, X-ray, spectroscopic and a preliminary Suzuki coupling screening studies of a complete series of dPPfMX2 (M = Pt, Pd; X = Cl, Br, I) [J].
Colacot, TJ ;
Qian, H ;
Cea-Olivares, R ;
Hernandez-Ortega, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 637 :691-697
[9]   Precious metal-phosphine complexes for homogeneous catalysis:: Synthesis and characterization of a complete series of Cp2Fe(PPh2)2MX2 (M = Pt, Pd; X = Cl, Br, I, Ph) [J].
Colacot, TJ ;
Fair, RJ ;
Boyko, WJ .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 144 :49-52
[10]   The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724