Rhodium-Catalyzed [2+2+2] Cycloaddition of Diynes with Carbodiimides and Carbon Dioxide under Ambient Conditions

被引:35
作者
Ishii, Masahiro [1 ]
Mori, Fumiya [1 ]
Tanaka, Ken [1 ,2 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] ACT C, JST, Kawaguchi, Saitama 3320012, Japan
基金
日本科学技术振兴机构;
关键词
cycloaddition; carbodiimides; carbon dioxide; diynes; rhodium; ENANTIOSELECTIVE SYNTHESIS; ALKENYL ISOCYANATES; NICKEL(0)-CATALYZED CYCLOADDITION; AROMATIC-COMPOUNDS; ALKYNES; NICKEL; CONSTRUCTION; COMPLEXES; CYCLOTRIMERIZATION; ALPHA; OMEGA-DIYNES;
D O I
10.1002/chem.201304623
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It has been established that a cationic rhodium(I)/H-8-binap complex is able to catalyze the [2+2+2] cycloaddition of diynes with carbodiimides and carbon dioxide under ambient conditions. Enantio- and/or regioselective variants of these reactions are also disclosed.
引用
收藏
页码:2169 / 2174
页数:6
相关论文
共 92 条
[1]   Synthesis of hexahydropyrrolo[2,3-b]indole alkaloids based on the aza-Pauson-Khand-type reaction of alkynecarbodiimides [J].
Aburano, Daisuke ;
Yoshida, Tatsunori ;
Miyakoshi, Naoki ;
Mukai, Chisato .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6878-6884
[2]   SOME CATALYTIC PROPERTIES OF RH(DIPHOS) (ETA-BPH4) [J].
ALBANO, P ;
ARESTA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 190 (03) :243-246
[3]  
[Anonymous], 2011, Angew. Chem., Int. Ed. Engl, DOI DOI 10.1002/ANGE.201102010
[4]  
[Anonymous], 2004, RUTHENIUM ORGANIC SY
[5]  
[Anonymous], 2009, ANGEW CHEM, DOI DOI 10.1002/ANGE.200805455
[6]  
Aresta M., 2010, CARBON DIOXIDE CHEM
[7]   Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].
Boñaga, LVR ;
Zhang, HC ;
Moretto, AF ;
Ye, H ;
Gauthier, DA ;
Li, J ;
Leo, GC ;
Maryanoff, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485
[8]   Cobalt-mediated macrocyclizations.: Facile synthesis of 2-oxo pyridinophanes via [2+2+2] cycloaddition of α,ω-diynes and isocyanates [J].
Boñaga, LVR ;
Zhang, HC ;
Gauthier, DA ;
Reddy, I ;
Maryanoff, BE .
ORGANIC LETTERS, 2003, 5 (24) :4537-4540
[9]   REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].
BRAUNSTEIN, P ;
MATT, D ;
NOBEL, D .
CHEMICAL REVIEWS, 1988, 88 (05) :747-764
[10]  
Broere D. L. J., 2012, SYNTHESIS-STUTTGART, P2639