Palladated Kaiser oxime resin as precatalyst for the Heck reaction in organic and aqueous media

被引:35
作者
Alacid, Emilio
Najera, Carmen
机构
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
[2] Univ Alicante, Inst Sintesis Organ, Alicante 03080, Spain
关键词
Heck reaction; palladacycles; polymers; alkenes; arylation;
D O I
10.1055/s-2006-951521
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A particular Kaiser oxime resin derived palladacycle is an efficient precatalyst for the Heck reaction with aryl iodides and bromides in DMF and in aqueous solvents under relatively moderate temperatures (110 degrees C and 120 degrees C) and high TON up to 10(5). Poisoning studies indicate that this polymer acts as a precatalyst. The polymer has been reused after recycling with low to moderate leaching of Pd(0).
引用
收藏
页码:2959 / 2964
页数:6
相关论文
共 34 条
[1]   Solvent-less and fluoride-free hiyama reaction of arylsiloxanes with aryl bromides and chlorides promoted by sodium hydroxide:: A useful protocol for palladium recycling and product isolation [J].
Alacid, Emilio ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :945-952
[2]   Oxime palladacycles revisited:: Stone-stable complexes nonetheless very active catalysts [J].
Alacid, Emilio ;
Alonso, Diego A. ;
Botella, Luis ;
Najera, Carmen ;
Pacheco, M. Carmen .
CHEMICAL RECORD, 2006, 6 (03) :117-132
[3]   Synthetic applications of oxime-derived palladacycles as versatile catalysts in cross-coupling reactions [J].
Alonso, DA ;
Botella, L ;
Nájera, C ;
Pacheco, C .
SYNTHESIS-STUTTGART, 2004, (10) :1713-1718
[4]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[5]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[6]   Synthesis of ynones by palladium-catalyzed acylation of terminal alkynes with acid chlorides [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (05) :1615-1619
[7]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[8]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[9]  
Alonso DA, 2002, ADV SYNTH CATAL, V344, P172, DOI 10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO
[10]  
2-9