Water-soluble palladacycles as precursors to highly recyclable catalysts for the suzuki coupling of aryl bromides in aqueous solvents

被引：119
作者：
Huang, Rongcai
Shaughnessy, Kevin H.
机构：
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
[2] Univ Alabama, Ctr Green Mfg, Tuscaloosa, AL 35487 USA
来源：
ORGANOMETALLICS | 2006年 / 25卷 / 17期
关键词：
D O I：
10.1021/om050940y
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A family of water-soluble palladacycles was prepared from benzylamine or benzaldehyde imine ligands bearing hydrophilic functional groups. The palladacycles derived from N,N-dimethyl-p-hydroxybenzylamine (7) and sodium 4-(N-benzylideneamino) benzenesulfonate (10) gave active catalysts for the Suzuki coupling of aryl bromides and activated aryl chlorides in combination with (2-di-tert-butylphosphinoethyl)trimethylammonium chloride (t-Bu-Amphos). The catalyst derived from 10/t-Bu-Amphos could be used for 12 reaction cycles in the Suzuki coupling of 4-bromotoluene at 80 degrees C before a significant loss of catalyst activity was observed.
引用
收藏
页码：4105 / 4112
页数：8
相关论文
共 45 条
[1]   Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water [J].
Baleizao, C ;
Corma, A ;
García, H ;
Leyva, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :439-446
[2]   Di- and tri-alkylphosphine adducts of S-donor palladacycles as catalysts in the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Scordia, EJM .
DALTON TRANSACTIONS, 2004, (22) :3864-3868
[3]   Orthopalladated phosphinite complexes as high-activity catalysts for the Suzuki reaction [J].
Bedford, RB ;
Hazelwood, SL ;
Horton, PN ;
Hursthouse, MB .
DALTON TRANSACTIONS, 2003, (21) :4164-4174
[4]   Phosphine and arsine adducts of N-donor palladacycles as catalysts in the Suzuki coupling of aryl bromides [J].
Bedford, RB ;
Cazin, CSJ ;
Coles, SJ ;
Gelbrich, T ;
Hursthouse, MB ;
Scordia, VJM .
DALTON TRANSACTIONS, 2003, (17) :3350-3356
[5]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[6]   High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source [J].
Bedford, RB ;
Cazin, CSJ ;
Coles, SJ ;
Gelbrich, T ;
Horton, PN ;
Hursthouse, MB ;
Light, ME .
ORGANOMETALLICS, 2003, 22 (05) :987-999
[7]  
Bedford RB, 2002, ANGEW CHEM INT EDIT, V41, P4120, DOI 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO
[8]  
2-7
[9]   Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reaction [J].
Bedford, RB ;
Welch, SL .
CHEMICAL COMMUNICATIONS, 2001, (01) :129-130
[10]   Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction? [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Pike, KJ ;
Wimperis, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) :173-181
12345