Synthesis of dendrimers terminated by bis(diphenylphosphinomethyl)amino ligands and use of their palladium complexes for catalyzing C-C cross-coupling reactions

被引:43
作者
Servin, Paul [1 ]
Laurent, Regis [1 ]
Romerosa, Antonio [2 ]
Peruzzini, Maurizio [3 ]
Majoral, Jean-Pierre [1 ]
Caminade, Anne-Marie [1 ]
机构
[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse 4, France
[2] Univ Almeria, Fac Ciencias Expt, Area Quim Inorgan, Almeria 04071, Spain
[3] Ist Chim Composti Organometall, ICCOM, CNR, I-50019 Sesto Fiorentino, Italy
关键词
D O I
10.1021/om800008p
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of two new series of phosphorus-containing dendrimers capped by bis(diphenylphosphinomethyl)amino groups linked to either tyramine or L-tyrosine methyl ester is reported up to the third generation (48 end groups). The corresponding complexes obtained in situ by reaction with Pd(OAc)(2) are used as catalysts in three types of C-C cross-coupling reactions, namely, Suzuki, Sonogashira, and Heck reactions, in the presence of water. A slightly positive dendritic effect is observed in the case of the Sonogashira reaction: the conversion increases when the generation (size and number of end groups) of the dendritic catalyst increases. In all cases, the series built from tyramine is more efficient than the series built from L-tyrosine, showing the influence of the local hindrance, and the dendrimers are generally more efficient than the corresponding monomers.
引用
收藏
页码:2066 / 2073
页数:8
相关论文
共 53 条
[1]   Introduction of the cluster fragment Ru3(CO)11 at the periphery of phosphine dendrimers catalyzed by the electron-reservoir complex [FeICp(C6Me6)] [J].
Alonso, E ;
Astruc, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3222-3223
[2]   Catalysts based on palladium dendrimers [J].
Andres, Roman ;
de Jesus, Ernesto ;
Carlos Flores, Juan .
NEW JOURNAL OF CHEMISTRY, 2007, 31 (07) :1161-1191
[3]  
[Anonymous], 2001, DENDRIMERS OTHER DEN
[4]   Solid-phase catalysis: A biomimetic approach toward ligands on dendritic arms to explore recyclable hydroformylation reactions [J].
Arya, P ;
Panda, G ;
Rao, NV ;
Alper, H ;
Bourque, SC ;
Manzer, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2889-2890
[5]   Metallodendritic catalysis for redox and carbon-carbon bond formation reactions:: A step towards green chemistry [J].
Astruc, D ;
Heuzé, K ;
Gatard, S ;
Méry, D ;
Nlate, S ;
Plault, L .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :329-338
[6]   Ruthenium hydride and dihydrogen complexes with dendrimeric multidentate ligands [J].
Bardaji, M ;
Caminade, AM ;
Majoral, JP ;
Chaudret, B .
ORGANOMETALLICS, 1997, 16 (15) :3489-3497
[7]   Phosphorus-containing dendrimers as multidentate ligands: Palladium, platinum, and rhodium complexes [J].
Bardaji, M ;
Kustos, M ;
Caminade, AM ;
Majoral, JP ;
Chaudret, B .
ORGANOMETALLICS, 1997, 16 (03) :403-410
[8]   Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes [J].
Batsanov, AS ;
Collings, JC ;
Fairlamb, IJS ;
Holland, JP ;
Howard, JAK ;
Lin, ZY ;
Marder, TB ;
Parsons, AC ;
Ward, RM ;
Zhu, J .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :703-706
[9]   Transition Metal Dendrimer Catalysts [J].
Berger, Alexsandro ;
Gebbink, Robertus J. M. Klein ;
van Koten, Gerard .
DENDRIMER CATALYSIS, 2006, 20 :1-38
[10]   Hydroformylation reactions using recyclable rhodium-complexed dendrimers on silica [J].
Bourque, SC ;
Alper, H ;
Manzer, LE ;
Arya, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :956-957