Gold as a catalyst. Part II. Alkynes in the reactions of carbon - carbon bond formation

被引:40
作者
Alyabyev, Sergey B. [1 ,3 ]
Beletskaya, Irina P. [2 ,4 ,5 ,6 ]
机构
[1] Eurasian Patent Org, Malyi Cherkasskii Per 2, Moscow 109012, Russia
[2] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1,Stroenie 3, Moscow 119991, Russia
[3] EAPO, Dept Chem & Med, Moscow, Russia
[4] MSU, Dept Chem, Moscow, Russia
[5] MSU, Dept Chem, Chem Sci, Moscow, Russia
[6] MSU, Dept Chem, Lab Organoelement Cpds, Moscow, Russia
关键词
UGI INTRAMOLECULAR HYDROARYLATION; INTERMOLECULAR 2+2 CYCLOADDITION; ONE-POT SYNTHESIS; GOLD(I)-CATALYZED TANDEM CYCLIZATION; AMINO-FUNCTIONALIZED SILICA; META-SUBSTITUTED PHENOLS; C-H BONDS; CLAISEN REARRANGEMENT; ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES;
D O I
10.1070/RCR4815
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This publication continues the series of reviews devoted to the current state of gold catalysis in organic chemistry. The second review addresses Au-catalyzed reactions of alkynes, giving rise to carbon -carbon bonds. Most of the described reactions are addition reactions involving the triple bond of alkynes. The review covers both intramolecular reactions, including cyclization of various substrates (enynes, diynes, enediynes, etc.) and enyne isomerization without ring formation, and intermolecular reactions, including alkyne reactions with alkenes, other alkynes, heteroaromatic compounds, etc., in particular, tandem reactions. A special part is devoted to dual gold catalysis involving the intermediate formation of binuclear complexes with a- and it-coordinated metal atoms. The last part of the review deals with the carbon -carbon bond formation reactions in which the alkyne triple bond is retained.
引用
收藏
页码:984 / 1047
页数:64
相关论文
共 371 条
[21]   Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].
Brenzovich, William E., Jr. ;
Benitez, Diego ;
Lackner, Aaron D. ;
Shunatona, Hunter P. ;
Tkatchouk, Ekaterina ;
Goddard, William A., III ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522
[22]   Gold(I)-Catalyzed Asymmetric Cyclopropenation of Internal Alkynes [J].
Briones, John F. ;
Davies, Huw M. L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :11916-11919
[23]   Rh2(S-PTAD)4-catalyzed asymmetric cyclopropenation of aryl alkynes [J].
Briones, John F. ;
Davies, Huw M. L. .
TETRAHEDRON, 2011, 67 (24) :4313-4317
[24]   Cationic Gold(I) π-Complexes of Terminal Alkynes and Their Conversion to Dinuclear σ,π-Acetylide Complexes [J].
Brown, Timothy J. ;
Widenhoefer, Ross A. .
ORGANOMETALLICS, 2011, 30 (21) :6003-6009
[25]   Cyclization of Gold Acetylides: Synthesis of Vinyl Sulfonates via Gold Vinylidene Complexes [J].
Bucher, Janina ;
Wurm, Thomas ;
Nalivela, Kumara Swamy ;
Rudolph, Matthias ;
Rominger, Frank ;
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) :3854-3858
[26]   Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615
[27]   Gold-catalyzed cyclizations of 1,7-enynes [J].
Cabello, Noemi ;
Rodriguez, Cristina ;
Echavarren, Antonio M. .
SYNLETT, 2007, (11) :1753-1758
[28]   Gold(I)-Catalyzed Polycyclization of Linear Dienediynes to Seven-Membered Ring-Containing Polycycles via Tandem Cyclopropanation/Cope Rearrangement/C-H Activation [J].
Cai, Pei-Jun ;
Wang, Yi ;
Liu, Cheng-Hang ;
Yu, Zhi-Xiang .
ORGANIC LETTERS, 2014, 16 (22) :5898-5901
[29]   A Recyclable Polystyrene-Supported Gold(I) Catalyst [J].
Cao, Wenjie ;
Yu, Biao .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1903-1907
[30]   Luminescent Homo- and Heteropolynuclear Gold Complexes Stabilized by a Unique Acetylide Fragment [J].
Carmen Blanco, M. ;
Camara, Jessica ;
Concepcion Gimeno, M. ;
Jones, Peter G. ;
Laguna, Antonio ;
Lopez-de-Luzuriaga, Jose M. ;
Elena Olmos, M. ;
Dolores Villacampa, M. .
ORGANOMETALLICS, 2012, 31 (07) :2597-2605