Gold-catalysed reactions of diynes

被引：406

作者：

Asiri, Abdullah M. ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

[2] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

CHEMICAL SOCIETY REVIEWS | 2016年 / 45卷 / 16期

关键词：

ONE-POT SYNTHESIS; HIGHLY EFFICIENT ACCESS; GAMMA-ALKYNOIC ACIDS; TERMINAL ALKYNES; CASCADE CYCLIZATION; GOLD(I)-CATALYZED CYCLOISOMERIZATION; HYDRATIVE CYCLIZATION; FURAN-YNE; AU(I)-CATALYZED CYCLOISOMERIZATION; SELECTIVE CYCLOISOMERIZATION;

D O I：

10.1039/c6cs00023a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this critical review the reactivity patterns observed with different types of diyne substrates in gold catalysis are discussed. Apart from the many examples from homogeneous catalysis, the few examples from heterogeneous gold catalysis are also included. With a proper arrangement of the two alkynes unique and exciting reactivity patterns like 1,3-carbonyl transpositions, carbene transfer reactions, cascade annulations, macrocyclisations or the formation of gold vinylidene intermediates are observed. These reactions are of interest for organic synthesis, for pharmaceutical and medicinal chemistry and for material science.

引用

页码：4471 / 4503

页数：33

共 210 条

[1] [3,3]-Sigmatropic Rearrangement Step in the Gold-Catalyzed Cyclization of Allyl-(ortho-alkinylphenyl)methyl Ethers [J].

Ackermann, Martin ;

Bucher, Janina ;

Rappold, Melissa ;

Graf, Katharina ;

Rominger, Frank ;

Hashmi, A. Stephen K. .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (08) :1786-1794

[2] Gold-catalyzed bis-cyclization of 1,2-diol- or acetonide-tethered alkynes. Synthesis of β-lactam-bridged acetals: a combined experimental and theoretical study [J].

Alcaide, Benito ;

Almendros, Pedro ;

Carrascosa, Rocio ;

Lopez, Ramon ;

Menendez, Maria I. .

TETRAHEDRON, 2012, 68 (52) :10748-10760

[3] Gold-catalyzed direct cycloketalization of acetonide-tethered alkynes in the presence of water [J].

Alcaide, Benito ;

Almendros, Pedro ;

Carrascosa, Rocio .

TETRAHEDRON, 2012, 68 (46) :9391-9396

[4]

[Anonymous], 2015, SYNTHESIS

[5] AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].

Asao, N ;

Sato, K ;

Menggenbateer ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685

[6] AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo) benzene and benzyne [J].

Asao, Naoki ;

Sato, Kenichiro .

ORGANIC LETTERS, 2006, 8 (23) :5361-5363

[7] Gold-Catalyzed Rearrangements: Reaction Pathways Using 1-Alkenyl-2-alkynylcyclopropane Substrates [J].

Barluenga, Jose ;

Tudela, Eva ;

Vicente, Ruben ;

Ballesteros, Alfredo ;

Tomas, Miguel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :2107-2110

[8] Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation [J].

Barrett, Matthew J. ;

Davies, Paul W. ;

Grainger, Richard S. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) :8676-8686

[9] Gold-catalyzed cycloisomerization of alk-4-yn-1-ones [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (06) :1221-1225

[10] Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition-Cyclization-Elimination Cascade [J].

Blanc, Aurelien ;

Tenbrink, Katharina ;

Weibel, Jean-Marc ;

Pale, Patrick .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5342-5348

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