A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles

被引:207
作者
Billingsley, Kelvin L. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
C-C coupling; nitrogen heterocycles; palladium; Suzuki-Miyaura coupling;
D O I
10.1002/anie.200801465
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) One of the most general systems for the cross-coupling of aryl and heteroaryl bromides and chlorides with 2-pyridyl-derived nucleophiles has been developed, for which catalysts comprising [Pd2(dba)3] and either diaryl (1) or dialkyl phosphine oxide (2) supporting ligands were found to be ideal (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4695 / 4698
页数:4
相关论文
共 36 条
[1]   Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].
Ackermann, L ;
Born, R ;
Spatz, JH ;
Meyer, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219
[2]  
Ackermann L., 2005, ANGEW CHEM, V117, P7382
[3]   Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates [J].
Ackermann, Lutz ;
Althammer, Andreas .
ORGANIC LETTERS, 2006, 8 (16) :3457-3460
[4]  
AHMAN B, 2002, Patent No. 02094815
[5]   Pyrrolopyridine inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2) [J].
Anderson, David R. ;
Meyers, Marvin J. ;
Vernier, William F. ;
Mahoney, Matthew W. ;
Kurumbail, Ravi G. ;
Caspers, Nicole ;
Poda, Gennadiy I. ;
Schindler, John F. ;
Reitz, David B. ;
Mourey, Robert J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (11) :2647-2654
[6]  
[Anonymous], [No title captured]
[7]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[8]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[9]   Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].
Billingsley, Kelvin ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366
[10]   Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling [J].
Bouillon, A ;
Lancelot, JC ;
Santos, JSD ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2003, 59 (50) :10043-10049