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
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
[21]  
Botella L, 2002, ANGEW CHEM INT EDIT, V41, P179, DOI 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO
[22]  
2-O
[23]   PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA [J].
CASALNUOVO, AL ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4324-4330
[24]   Air- and moisture-stable cyclopalladated complexes as efficient catalysts for Suzuki-Miyaura coupling reaction [J].
Chen, CL ;
Liu, YH ;
Peng, SM ;
Liu, ST .
ORGANOMETALLICS, 2005, 24 (06) :1075-1081
[25]   An efficient catalyst for Suzuki-Miyaura coupling reaction in aqueous medium under aerobic conditions [J].
Chen, CL ;
Liu, YH ;
Peng, SM ;
Liu, ST .
TETRAHEDRON LETTERS, 2005, 46 (03) :521-523
[26]   Kinetics and mechanistic aspects of the Heck reaction promoted by a CN-palladacycle [J].
Consorti, CS ;
Flores, FR ;
Dupont, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :12054-12065
[27]   ELECTROPHILIC AROMATIC SUBSTITUTION REACTIONS BY PLATINUM(2) AND PALLADIUM(2) CHLORIDES ON N,N-DIMETHYLBENZYLAMINES [J].
COPE, AC ;
FRIEDRICH, EC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (04) :909-+
[28]   Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines [J].
DeVasher, RB ;
Moore, LR ;
Shaughnessy, KH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7919-7927
[29]   Experimental and computational study of steric and electronic effects on the coordination of bulky, water-soluble alkylphosphines to palladium under reducing conditions: Correlation to catalytic [J].
DeVasher, RB ;
Spruell, JM ;
Dixon, DA ;
Broker, GA ;
Griffin, ST ;
Rogers, RD ;
Shaughnessy, KH .
ORGANOMETALLICS, 2005, 24 (05) :962-971
[30]   The art of meeting palladium specifications in active pharmaceutical ingredients produced by Pd-catalyzed reactions [J].
Garrett, CE ;
Prasad, K .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (08) :889-900