High-Oxidation-State Palladium Catalysis: New Reactivity for Organic Synthesis

被引:452
作者
Muniz, Kilian [1 ]
机构
[1] Univ Strasbourg, Inst Chim, UMR 7177, F-67000 Strasbourg, France
关键词
coupling reactions; elimination; homogeneous catalysis; oxidation states; palladium; CROSS-COUPLING REACTIONS; C-H FUNCTIONALIZATION; X-RAY-STRUCTURE; REDUCTIVE ELIMINATION; BOND FORMATION; N-FLUOROBENZENESULFONIMIDE; ORGANOMETALLIC CHEMISTRY; CYCLIZATION-OXIDATION; HYDROGEN-PEROXIDE; CRYSTAL-STRUCTURE;
D O I
10.1002/anie.200903671
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recent years have seen the rapid development of a new field of palladium catalysis in organic synthesis. This chemistry takes place outside the usually encountered Pd0PdII cycles. It is characterized by the presence of strong oxidants, which prevent further palladium(II)promoted reactions at a given point of the catalytic cycle by selective metal oxidation. The resulting higher-oxidation-state palladium complexes have been used to develop a series of new synthetic transformations that cannnot be realized within conventional palladium catalysis. This type of catalysis by palladium in a higher oxidation state is of significant synthetic potential. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9412 / 9423
页数:12
相关论文
共 133 条
[21]   Oxidation of diorganopalladium(II) complexes by water and halogens: Reactions involving methyl group transfer and structural studies of hydrogen-bonded adducts formed by aryl alcohols with the pallada(IV)cyclopentane complex Pd(CH2CH2CH2CH2)(OH){(pz)(3)BH}([(pz)(3)BH](-)=tris(pyrazol-1-yl)borate) [J].
Canty, AJ ;
Jin, H ;
Roberts, AS ;
Skelton, BW ;
White, AH .
ORGANOMETALLICS, 1996, 15 (26) :5713-5722
[22]   DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].
CANTY, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90
[23]   Oxidation of complexes by (O2CPh)2 and (ER)2 (E = S, Se), including structures of Pd(CH2CH2CH2CH2)(SePh)2(bpy) (bpy = 2,2′-bipyridine) and MMe2(SePh)2(L2) (M = Pd, Pt; L2 = bpy, 1,10-phenanthroline) and C•••O and C•••E bond formation at palladium(IV) [J].
Canty, AJ ;
Jin, H ;
Skelton, BW ;
White, AH .
INORGANIC CHEMISTRY, 1998, 37 (16) :3975-3981
[24]   OXIDATION REACTIONS USING WATER, HYDROGEN-PEROXIDE AND HALOGENS TO GIVE PALLAD(IV)CYCLOPENTANE COMPLEXES PDX(C4H8)((PZ)(3)BH) (X=OH, CL, BR, I) - THE CRYSTAL-STRUCTURE OF THE HYDROXOPLATINUM(IV) COMPLEX PT(OH) ME(2)((PZ)(3)BH), FORMED BY USE OF WATER AS AN OXIDANT [J].
CANTY, AJ ;
FRITSCHE, SD ;
JIN, H ;
SKELTON, BW ;
WHITE, AH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 490 (1-2) :C18-C19
[25]   Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].
Cárdenas, DJ ;
Martín-Matute, B ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040
[26]  
Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
[27]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313
[28]   CONFORMATIONAL EFFECTS IN ELEMENTARY STEPS IN CATALYTIC REACTIONS - OXIDATIVE ADDITION OF 3-BROMOPROP-1-ENE TO A PALLADIUM(II) METALLACYCLIC COMPLEX [J].
CATELLANI, M ;
MANN, BE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 390 (02) :251-255
[29]  
CATELLANI M, 1994, ANGEW CHEM INT EDIT, V33, P2421
[30]  
CATELLANI M, 1994, ANGEW CHEM, V106, P2559