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
[1]   Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines [J].
Abbiati, G ;
Arcadi, A ;
Bianchi, G ;
Di Giuseppe, S ;
Marinelli, F ;
Rossi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6959-6966
[2]   Versatile Synthesis of Polyfunctionalized Carbazoles from (3-Iodoindol-2-yl)butynols via a Gold-Catalyzed Intramolecular Iodine-Transfer Reaction [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Busto, Eduardo ;
Fernandez, Israel ;
Pilar Ruiz, M. ;
Xiaokaiti, Gulinigaer .
ACS CATALYSIS, 2015, 5 (06) :3417-3421
[3]   Gold-Catalyzed Cyclizations of Alkynol-Based Compounds: Synthesis of Natural Products and Derivatives [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. .
MOLECULES, 2011, 16 (09) :7815-7843
[4]   Heterogeneous Catalytic Homocoupling of Terminal Alkynes [J].
Alonso, Francisco ;
Yus, Miguel .
ACS CATALYSIS, 2012, 2 (07) :1441-1451
[5]   Gold as a catalyst. Part I. Nucleophilic addition to the triple bonds [J].
Alyabyev, Sergey B. ;
Beletskaya, Irina P. .
RUSSIAN CHEMICAL REVIEWS, 2017, 86 (08) :689-749
[6]  
[Anonymous], 1994, Patent WO, Patent No. 1994004525
[7]   Gold-Catalyzed Dearomative Spirocyclization of Aryl Alkynoate Esters [J].
Aparece, Mark D. ;
Vadola, Paul A. .
ORGANIC LETTERS, 2014, 16 (22) :6008-6011
[8]   Gold-catalysed direct couplings of indoles and pyrroles with 1,3-dicarbonyl compounds [J].
Arcadi, A ;
Alfonsi, M ;
Bianchi, G ;
D'Anniballe, G ;
Marinelli, F .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :331-338
[9]   Gold-catalysed reactions of diynes [J].
Asiri, Abdullah M. ;
Hashmi, A. Stephen K. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4471-4503
[10]   A TOTAL SYNTHESIS OF PROSTAGLANDIN E1 AND RELATED SUBSTANCES VIA ENDO-BICYCLOHEXANE INTERMEDIATES [J].
AXEN, U ;
LINCOLN, FH ;
THOMPSON, JL .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (06) :303-&