Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates

被引:71
作者
Ackermann, Lutz [1 ]
Kapdi, Anant R. [1 ]
Fenner, Sabine [1 ]
Kornhaass, Christoph [1 ]
Schulzke, Carola [2 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Trinity Coll Dublin, Sch Chem, Dublin 2, Ireland
关键词
catalysis; cross-coupling; ligand; palladium; tosylate; H BOND ACTIVATION; CATALYZED DIRECT ARYLATIONS; C-H; PHOSPHINOUS ACID; SUZUKI-MIYAURA; ARYL CHLORIDES; GRIGNARD-REAGENTS; HALOGENATED NITROGEN; INDOLE SYNTHESES; CARBON-OXYGEN;
D O I
10.1002/chem.201002386
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) pre-ligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.
引用
收藏
页码:2965 / 2971
页数:7
相关论文
共 108 条
[61]   DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement [J].
Ishikawa, Shunpei ;
Manabe, Kei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :772-775
[62]   Transition Metal-Catalysed, Direct and Site-Selective N1-, C2-or C3-Arylation of the Indole Nucleus: 20 Years of Improvements [J].
Joucla, Lionel ;
Djakovitch, Laurent .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) :673-714
[63]   Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds [J].
Kakiuchi, F ;
Usui, M ;
Ueno, S ;
Chatani, N ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2706-2707
[64]   Three-component indole synthesis using ortho-dihaloarenes [J].
Kaspar, LT ;
Ackermann, L .
TETRAHEDRON, 2005, 61 (48) :11311-11316
[65]   Preparation of enamides via palladium-catalyzed amidation of enol tosylates [J].
Klapars, A ;
Campos, KR ;
Chen, CY ;
Volante, RP .
ORGANIC LETTERS, 2005, 7 (06) :1185-1188
[66]   Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes [J].
Lerebours, R ;
Camacho-Soto, A ;
Wolf, C .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8601-8604
[67]   Palladium(II)-catalyzed conjugate addition of arylsiloxanes in water [J].
Lerebours, Rachel ;
Wolf, Christian .
ORGANIC LETTERS, 2007, 9 (14) :2737-2740
[68]   Chemoselective nucleophilic arylation and single-step oxidative esterification of aldehydes using siloxanes and a palladium-phosphinous acid as a reaction switch [J].
Lerebours, Rachel ;
Wolf, Christian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13052-13053
[69]  
Li G. Y., 2001, ANGEW CHEM, V113, P1561
[70]   Highly active, air-stable palladium catalysts for the C-C and C-S bond-forming reactions of vinyl and aryl chlorides:: Use of commercially available [(t-Bu)2P(OH)]2PdCl2, [(t-Bu)2P(OH)PdCl2]2, and [[(t-Bu)2PO•••H•••OP(t-Bu)2]PdCl]2 as catalysts [J].
Li, GY .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3643-3650