Oxime palladacycles revisited:: Stone-stable complexes nonetheless very active catalysts

被引:108
作者
Alacid, Emilio
Alonso, Diego A.
Botella, Luis
Najera, Carmen
Pacheco, M. Carmen
机构
[1] Univ Alicante, Dept Quim Organ, Fac Ciencias, E-03080 Alicante, Spain
[2] Univ Alicante, Inst Sintesis Organ, Fac Ciencias, E-03080 Alicante, Spain
关键词
palladacycle; oxime; nanoparticles; catalysis; cross coupling;
D O I
10.1002/tcr.20077
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Our review critically presents the main achievements, advantages, and limitations of oxime palladacycles as high-turnover catalysts for Heck, as well as homo- and cross-coupling reactions such as Suzuki-Miyaura, Stille, Ullmann-type, Cassar-Heck-Sonogashira, sila-Sonogashira, Glaser-type, Hiyama, and alkoxycarbonylation reactions. New developments in this area are reviewed from a mechanistic and synthetic point of view. The role of oxime palladacycles as a source of highly active zero-valent palladium species is also discussed. (c) 2006 The Japan Chemical journal Forum and Wiley Periodicals, Inc.
引用
收藏
页码:117 / 132
页数:16
相关论文
共 104 条
[11]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[12]   FUNCTIONALIZATION OF UNACTIVATED METHYL-GROUPS THROUGH CYCLOPALLADATION REACTIONS [J].
BALDWIN, JE ;
JONES, RH ;
NAJERA, C ;
YUS, M .
TETRAHEDRON, 1985, 41 (04) :699-711
[13]   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
[14]   The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].
Bedford, RB ;
Cazin, CSJ ;
Holder, D .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321
[15]   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
[16]   Orthopalladated and -platinated bulky triarylphosphite complexes: Synthesis, reactivity and application as high-activity catalysts for Suzuki and Stille coupling reactions [J].
Bedford, RB ;
Hazlewood, SL ;
Limmert, ME ;
Albisson, DA ;
Draper, SM ;
Scully, PN ;
Coles, SJ ;
Hursthouse, MB .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3216-3227
[17]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[18]   Platinum catalysts for Suzuki biaryl coupling reactions [J].
Bedford, RB ;
Hazelwood, SL ;
Albisson, DA .
ORGANOMETALLICS, 2002, 21 (13) :2599-2600
[19]   Extremely high activity catalysts for the Suzuki coupling of aryl chlorides: the importance of catalyst longevity [J].
Bedford, RB ;
Hazelwood, SL ;
Limmert, ME .
CHEMICAL COMMUNICATIONS, 2002, (22) :2610-2611
[20]  
Bedford RB, 2002, ANGEW CHEM INT EDIT, V41, P4120, DOI 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO