Tunable Palladium-FibreCats for Aryl Chloride Suzuki Coupling with Minimal Metal Leaching

被引:38
作者
Colacot, Thomas J. [1 ]
Carole, William A. [1 ]
Neide, Bruce A. [1 ]
Harad, Ajay [1 ]
机构
[1] Johnson Matthey Catalysis & Chiral Technol, W Deptford, NJ 08066 USA
关键词
D O I
10.1021/om800047y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A very convenient general method was developed for making tunable polypropylene-supported Pd complexes of electron-rich and bulky monodentate ligands such as Q-Phos, t-Bu3P, (Me2NC6H4)P(t-Bu)(2) (A(ta)-Phos), and IPr-carbene as well as bidentate ligands such as BINAP, dppf, and dippf in 4-8% Pd loading. These catalysts have been utilized for Suzuki coupling of aryl chlorides and bromides with product conversions up to 100%. Minimal metal leaching has been observed in many cases. Many of these catalysts were recycled a few times in model systems with an undetected amount of Pd leaching.
引用
收藏
页码:5605 / 5611
页数:7
相关论文
共 51 条
[11]   Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions [J].
Crudden, CM ;
Sateesh, M ;
Lewis, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :10045-10050
[12]   Are heterogeneous catalysts precursors to homogeneous catalysts? [J].
Davies, IW ;
Matty, L ;
Hughes, DL ;
Reider, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) :10139-10140
[13]   A highly practical and general route for α-arylations of ketones using bis-phosphinoferrocene-based palladium catalysts [J].
Grasa, Gabriela A. ;
Colacot, Thomas J. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (03) :522-529
[14]   α-arylation of ketones using highly active, air-stable (DtBPF)PdX2 (X = cl, br) catalysts [J].
Grasa, Gabriela A. ;
Colacot, Thomas J. .
ORGANIC LETTERS, 2007, 9 (26) :5489-5492
[15]   TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES [J].
GRUSHIN, VV ;
ALPER, H .
CHEMICAL REVIEWS, 1994, 94 (04) :1047-1062
[16]   New air-stable catalysts for general and efficient Suzuki-Miyaura cross-coupling reactions of heteroaryl chlorides [J].
Guram, AS ;
King, AO ;
Allen, JG ;
Wang, XH ;
Schenkel, LB ;
Chan, J ;
Bunel, EE ;
Faul, MM ;
Larsen, RD ;
Martinelli, MJ ;
Reider, PJ .
ORGANIC LETTERS, 2006, 8 (09) :1787-1789
[17]   Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides [J].
Hooper, MW ;
Utsunomiya, M ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2861-2873
[18]   Pd-Smopex-111: A new catalyst for Heck and Suzuki cross-coupling reactions [J].
Jiang, Xinglong ;
Sclafani, Joseph ;
Prasad, Kapa ;
Repic, Oljan ;
Blacklock, Thomas J. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (04) :769-772
[19]   Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings [J].
Kataoka, N ;
Shelby, Q ;
Stambuli, JP ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5553-5566
[20]   Activation of aryl chlorides for Suzuki cross-coupling by ligandless, heterogeneous palladium [J].
LeBlond, CR ;
Andrews, AT ;
Sun, YK ;
Sowa, JR .
ORGANIC LETTERS, 2001, 3 (10) :1555-1557