Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts

被引:47
作者
Beletskaya, IP [1 ]
Davydov, DV [1 ]
Gorovoy, MS [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia
关键词
5-aryltetrazoles; arylation; Pd-catalysis regioselectivity; iodonium salts; Cu(II);
D O I
10.1016/S0040-4039(02)01325-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium(0)-catalyzed arylation of 5-aryltetrazoles in t-BuOH at 80degreesC with diaryliodonium salts proceeds in the presence of copper(II) phenylcyclopropyl carboxylate regioselectively at the N2 position. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6221 / 6223
页数:3
相关论文
共 13 条
[1]   ARYLATION OF TETRAZOLIDE WITH DIARYLIODONIUM HALIDES - EVIDENCE FOR INTERMEDIACY OF BENZYNE [J].
AKIYAMA, T ;
IMASAKI, Y ;
KAWANISI, M .
CHEMISTRY LETTERS, 1974, (03) :229-230
[2]  
Beletskaya IP, 1998, TETRAHEDRON LETT, V39, P5621, DOI 10.1016/S0040-4039(98)01063-6
[3]   Pd- and Cu-catalyzed selective arylation of benzotriazole [J].
Beletskaya, IP ;
Davydov, DV ;
Moreno-Mañas, M .
TETRAHEDRON LETTERS, 1998, 39 (31) :5617-5620
[4]  
DAVYDOV DV, 1999, 10 S ORG MET CHEM VE
[5]   N-phenylation of azole derivatives by triphenylbismuth derivatives cupric acetate [J].
Fedorov, AY ;
Finet, JP .
TETRAHEDRON LETTERS, 1999, 40 (14) :2747-2748
[6]   SYNTHESIS OF SOME TRIAZOLE, TETRAZOLE, AND TETRAZINE DERIVATIVES FROM N-BETA-NAPHTHALENESULFONYLBENZOHYDRAZIDOYL CHLORIDES [J].
HASSANEEN, HM ;
FAHMI, AA ;
ABDELHAMID, H ;
YASSIN, AA ;
SHAWALI, AS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (03) :797-800
[7]   SYNTHESIS OF 2,5-DIARYLTETRAZOLES FROM N-PHENYLSULFONYL-BENZHYDRAZIDOYL CHLORIDES AND ARYLHYDRAZINES [J].
ITO, S ;
TANAKA, Y ;
KAKEHI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (03) :762-766
[8]   FACILE SYNTHESIS OF 2,5-DISUBSTITUTED TETRAZOLES BY REACTION OF PHENYLSULFONYLHYDRAZONES WITH ARENEDIAZONIUM SALTS [J].
ITO, S ;
TANAKA, Y ;
KAKEHI, A ;
KONDO, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (07) :1920-1923
[9]  
Koldobskii G.I., 1994, Russ. Chem. Rev, V63, P797, DOI [10.1070/RC1994v063n10ABEH000119, DOI 10.1070/RC1994V063N10ABEH000119]
[10]   New aryl/heteroaryl C-N bond cross-coupling reactions via arylboronic acid cupric acetate arylation [J].
Lam, PYS ;
Clark, CG ;
Saubern, S ;
Adams, J ;
Winters, MP ;
Chan, DMT ;
Combs, A .
TETRAHEDRON LETTERS, 1998, 39 (19) :2941-2944