Synthesis of ortho-cyanopyridylboronic acids and esters toward cyano-functionalized bipyridines

被引:29
作者
Cailly, T [1 ]
Fabis, F [1 ]
Bouillon, A [1 ]
Lemaître, S [1 ]
Sopkova, J [1 ]
de Santos, O [1 ]
Rault, S [1 ]
机构
[1] Univ Caen Basse Normandie, UFR Sci Pharmaceut, UPRES EA 3915, Ctr Etud & Rech Medicament Normandie, F-14032 Caen, France
关键词
cross-coupling; lithiation; nitrites; boronic acids; bipyridines;
D O I
10.1055/s-2005-922772
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work describes the synthesis of ortho-cyanopy-ridylboronic acids and esters. Their reactivity with pyridine halides in the Suzuki cross-coupling reaction is evaluated and shows that the cyanopyridyl boronic esters appear to be more stable than their corresponding acids. These esters allowed us to synthesize new cyanobipyridine systems.
引用
收藏
页码:53 / 56
页数:4
相关论文
共 31 条
[1]   An efficient two-step total synthesis of the quaterpyridine nemertelline [J].
Bouillon, A ;
Voisin, AS ;
Robic, A ;
Lancelot, JC ;
Collot, V ;
Rault, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10178-10180
[2]   Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-halopyridin-4-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (22) :4369-4373
[3]   Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (17) :3323-3328
[4]   Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (14) :2885-2890
[5]   Effective lithiation of 3-bromopyridine: synthesis of 3-pyridine boronic acid and variously 3-substituted pyridines [J].
Cai, D ;
Larsen, RD ;
Reider, PJ .
TETRAHEDRON LETTERS, 2002, 43 (23) :4285-4287
[6]   Synthesis of ortho-substituted cyanopyridines through lithio intermediate trapping [J].
Cailly, T ;
Fabis, F ;
Lemaìtre, S ;
Bouillon, A ;
Rault, S .
TETRAHEDRON LETTERS, 2005, 46 (01) :135-137
[7]   Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates [J].
Chan, DMT ;
Monaco, KL ;
Li, RH ;
Bonne, D ;
Clark, CG ;
Lam, PYS .
TETRAHEDRON LETTERS, 2003, 44 (19) :3863-3865
[8]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[9]   Generation of 3-pyridyl biaryl systems via palladium-catalyzed Suzuki cross-couplings of aryl halides with 3-pyridylboroxin [J].
Cioffi, CL ;
Spencer, WT ;
Richards, JJ ;
Herr, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2210-2212
[10]  
FISCHER FC, 1974, RECL TRAV CHIM PAY B, V93, P21