COPPER-CATALYZED β-IODOVINYLATION OF AZOLE AND PYRROLE DERIVATIVES

被引:1
作者
Ricard, Simon [1 ]
Ladouceur, Francois [1 ]
Couture, Guillaume [1 ]
Daoust, Benoit [1 ]
机构
[1] Univ Quebec Trois Rivieres, Dept Chem Biochem & Phys, CP 500, Trois Rivieres, PQ G9A 5H7, Canada
关键词
N-ARYLATION; REGIOSELECTIVE SYNTHESIS; ARYL; EFFICIENT; MILD; VINYLATION; PALLADIUM; INDOLES; WATER; ACCESS;
D O I
10.3987/COM-20-14234
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein is described an efficient copper-catalyzed synthesis of beta-iodovinyl-azole and beta-iodovinyl-pyrrole derivatives using (E)-1,2-diiodoethene which was efficiently applied to azole and pyrrole derivatives in both organic and hydro-organic medium to afford the corresponding beta-iodovinylated adducts in up to excellent yields with complete stereocontrol. These nitrogenated vinyl iodides can be further functionalized into disubstituted olefins through various metal catalyzed coupling reactions.
引用
收藏
页码:747 / 767
页数:21
相关论文
共 56 条
[1]   Rhodium(I)-N-Heterocyclic Carbene Catalyst for Selective Coupling of N-Vinylpyrazoles with Alkynes via C-H Activation [J].
Azpiroz, Ramon ;
Rubio-Perez, Laura ;
Di Giuseppe, Andrea ;
Passarelli, Vincenzo ;
Lahoz, Fernando J. ;
Castarlenas, Ricardo ;
Perez-Torrente, Jesus J. ;
Oro, Luis A. .
ACS CATALYSIS, 2014, 4 (12) :4244-4253
[2]  
Bandini M., 2009, CATALYTIC FUNCTIONAL, V48
[3]   Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water [J].
Bollenbach, Maud ;
Aquino, Pedro G. V. ;
de Araujo-Junior, Joao Xavier ;
Bourguignon, Jean-Jacques ;
Bihel, Frederic ;
Salome, Christophe ;
Wagner, Patrick ;
Schmitt, Martine .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (55) :13676-13683
[4]   Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (04) :639-647
[5]   BASICITY AND ACIDITY OF AZOLES [J].
CATALAN, J ;
ABBOUD, JLM ;
ELGUERO, J .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1987, 41 :187-274
[6]   Synthesis of Polypeptides by Ring-Opening Polymerization of α-Amino Acid N-Carboxyanhydrides [J].
Cheng, Jianjun ;
Deming, Timothy J. .
PEPTIDE-BASED MATERIALS, 2012, 310 :1-26
[7]   Iron-catalyzed N-arylation of nitrogen nucleophiles [J].
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865
[8]   Mild conditions for copper-catalysed N-arylation of pyrazoles [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709
[9]   Recent Advances in the Synthesis of N-Containing Heteroaromatics via Heterogeneously Transition Metal Catalysed Cross-Coupling Reactions [J].
Djakovitch, Laurent ;
Batail, Nelly ;
Genelot, Marie .
MOLECULES, 2011, 16 (06) :5241-5267
[10]  
Fontana G., 2010, Curr. Bioact. Compd, V6, P284