Direct and improved access to unsymmetrically functionalized bipyridines by a Stille-type cross-coupling reaction

被引:11
作者
Mathieu, J [1 ]
Marsura, A [1 ]
机构
[1] UHP Nancy 1, UHP, CNRS, UMR 7565,Grp Etud Vecteurs Supramol Medicament, F-54001 Nancy, France
关键词
Stille-type reaction; bipyridines multigram scale synthesis;
D O I
10.1081/SCC-120015770
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Stille-type cross-coupling reaction on mesylate, tosylate, and triflate allowed synthesis of symmetrical but also interesting unsymmetrical monofunctionalized 2'2'-bipyridines in possible multigram scales.
引用
收藏
页码:409 / 414
页数:6
相关论文
共 10 条
[1]   Synthesis of pyridylstannanes from halopyridines and hexamethyldistannane with catalytic palladium. [J].
Benaglia, M ;
Toyota, S ;
Woods, CR ;
Siegel, JS .
TETRAHEDRON LETTERS, 1997, 38 (27) :4737-4740
[2]   NEW SYMMETRICAL AND UNSYMMETRIC POLYFUNCTIONALIZED 2,2'-BIPYRIDINES [J].
DEVAINS, JBR ;
PAPET, AL ;
MARSURA, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (04) :1069-1077
[3]   PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486
[4]  
Greene T.W., 1999, PROTECTIVE GROUPS OR, P779
[5]   Synthesis, structure, and properties of oligo-tridentate ligands; Covalently assembled precursors of coordination arrays [J].
Hanan, GS ;
Schubert, US ;
Volkmer, D ;
Riviere, E ;
Lehn, JM ;
Kyritsakas, N ;
Fischer, J .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (02) :169-182
[6]   Straightforward access to methyl-polyheterocycles from direct para-lithiation of 3-picoline [J].
Mathieu, J ;
Gros, P ;
Fort, Y .
TETRAHEDRON LETTERS, 2001, 42 (10) :1879-1881
[7]  
NEUMANN WP, 1970, ORGANIC CHEM TIN, P488
[8]  
PSYCHOGIOS N, COMMUNICATION
[9]   Efficient synthesis of 4-, 5-, and 6-methyl-2,2′-bipyridine by a Negishi cross-coupling strategy followed by high-yield conversion to bromo- and chloromethyl-2,2′-bipyridines [J].
Savage, SA ;
Smith, AP ;
Fraser, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10048-10051
[10]   Stille-type cross-coupling - An efficient way to various symmetrically and unsymmetrically substituted methyl-bipyridines: Toward new ATRP catalysts [J].
Schubert, US ;
Eschbaumer, C ;
Heller, M .
ORGANIC LETTERS, 2000, 2 (21) :3373-3376