Suzuki-Miyaura coupling reaction of aryl chlorides using di(2,6-dimethylmorpholino)phenylphosphine as ligand

被引:52
作者
Cho, Su-Dong
Kim, Ho-Kyun
Yim, Heung-seop
Kim, Mi-Ra
Lee, Jin-Kook [1 ]
Kim, Jeurn-Jong
Yoon, Yong-Jin
机构
[1] Pusan Natl Univ, Dept Polymer Sci & Engn, Pusan 609735, South Korea
[2] Gyeongsang Natl Univ, Dept Chem, Jinju 660701, South Korea
[3] Gyeongsang Natl Univ, Grad Sch Mol Mat & Nanochem, Jinju 660701, South Korea
[4] Pusan Natl Univ, Ctr Plast Informat Syst, Pusan 609735, South Korea
[5] Gyeongsang Natl Univ, Dept Chem & Environm Biotechnol, Natl Core Res Ctr, Grad Sch Mol Mat & Nanochem, Jinju 660701, South Korea
关键词
Suzuki-Miyaura coupling; Pd-catalyzed coupling of aryl chlorides; PN2; ligand; C-C coupling reaction;
D O I
10.1016/j.tet.2006.12.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Suzuki-Miyaura coupling was achieved on a variety of aryl chlorides by using di(2,6-dimethylmorpholino)phenylphosphine (Ll) as a bulky electron-rich monoaryl phosphine ligand. We report the couplings of various chlorobenzenes and heteroaryl chlorides. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1345 / 1352
页数:8
相关论文
共 57 条
[1]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[2]   Homogeneous catalysts supported on soluble polymers: Biphasic Suzuki-Miyaura coupling of aryl chlorides using phase-tagged palladium-phosphine catalysts [J].
an der Heiden, M ;
Plenio, H .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1789-1797
[3]   A reassessment of the transition-metal free Suzuki-type coupling methodology [J].
Arvela, RK ;
Leadbeater, NE ;
Sangi, MS ;
Williams, VA ;
Granados, P ;
Singer, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168
[4]   Phenyl backbone-derived P,O- and P,N-ligands for palladium/ligand-catalyzed aminations of aryl bromides, iodides, and chlorides.: Syntheses and structures of (P,O)n-palladium(II)aryl(Br) complexes [J].
Bei, XH ;
Uno, T ;
Norris, J ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
ORGANOMETALLICS, 1999, 18 (10) :1840-1853
[5]   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
[6]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[7]  
2-N
[8]   Monoligated palladium species as catalysts in cross-coupling reactions [J].
Christmann, U ;
Vilar, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374
[9]   Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging suzuki coupling reactions [J].
Colacot, TJ ;
Shea, HA .
ORGANIC LETTERS, 2004, 6 (21) :3731-3734
[10]  
Collman J.P., 1987, PRINCIPLES APPL ORGA