Gold(III)-catalyzed three-component coupling reaction (TCC) selective toward furans.

An efficient three-component coupling reaction toward a variety of furan derivatives has been developed. This cascade transformation proceeds via the gold-catalyzed coupling reaction of phenylglyoxal derivatives, secondary amines, and terminal alkynes, under the reaction conditions, that undergoes cyclization into the furan core.

[1]  F. Rominger,et al.  Gold(I)-catalyzed rearrangement of 3-silyloxy-1,5-enynes: an efficient synthesis of benzo[b]thiophenes, dibenzothiophenes, dibenzofurans, and indole derivatives. , 2012, Chemistry.

[2]  T. Skrydstrup,et al.  Gold-catalyzed carbene transfer to alkynes: access to 2,4-disubstituted furans. , 2012, Angewandte Chemie.

[3]  F. Rominger,et al.  Gold(I)-catalyzed formation of benzo[b]furans from 3-silyloxy-1,5-enynes. , 2011, Angewandte Chemie.

[4]  J. Kang,et al.  Synthesis of substituted acetylenic epoxides followed by indium-catalyzed rearrangement to 2,3,5-trisubstituted furans. , 2011, The Journal of organic chemistry.

[5]  Huanfeng Jiang,et al.  Synthesis of 2,5-disubstituted 3-iodofurans via palladium-catalyzed coupling and iodocyclization of terminal alkynes. , 2011, The Journal of organic chemistry.

[6]  A. Hashmi Homogeneous gold catalysis beyond assumptions and proposals--characterized intermediates. , 2010, Angewandte Chemie.

[7]  Qiang Zhang,et al.  Gold-catalyzed three-component tandem process: an efficient and facile assembly of complex butenolides from alkynes, amines, and glyoxylic acid. , 2010, Journal of the American Chemical Society.

[8]  V. Gevorgyan,et al.  Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three Component Coupling Reaction. , 2010, Advanced synthesis & catalysis.

[9]  V. Gevorgyan,et al.  General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: one-pot synthesis of alpidem and zolpidem. , 2010, Angewandte Chemie.

[10]  S. Akai,et al.  Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: a practical route to furans and pyrroles. , 2009, Organic letters.

[11]  A. Aponick,et al.  An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols. , 2009, Organic letters.

[12]  I. Ubarretxena-Belandia,et al.  Water Soluble Phosphane-Gold(I) Complexes. Applications as Recyclable Catalysts in a Three-component Coupling Reaction and as Antimicrobial and Anticancer Agents. , 2009, European journal of inorganic chemistry.

[13]  A. Blanc,et al.  Silver(I)-catalyzed cascade: direct access to furans from alkynyloxiranes. , 2009, The Journal of organic chemistry.

[14]  C. Che,et al.  Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes , 2009 .

[15]  A. Corma,et al.  Supported gold(III) catalysts for highly efficient three-component coupling reactions. , 2008, Angewandte Chemie.

[16]  Zhuang-Ping Zhan,et al.  FeCl3-catalyzed nucleophilic substitution of propargylic acetates with enoxysilanes. , 2007, The Journal of organic chemistry.

[17]  Yuanhong Liu,et al.  Gold-catalyzed multicomponent synthesis of aminoindolizines from aldehydes, amines, and alkynes under solvent-free conditions or in water. , 2007, Organic letters.

[18]  V. Bansal,et al.  The first Au-nanoparticles catalyzed green synthesis of propargylamines via a three-component coupling reaction of aldehyde, alkyne and amine , 2007 .

[19]  M. Morreale,et al.  Room temperature zinc chloride-catalyzed cycloisomerization of Alk-3-yn-1-ones: synthesis of substituted furans. , 2007, Organic letters.

[20]  Junliang Zhang,et al.  Gold(I)-catalyzed reaction of 1-(1-alkynyl)-cyclopropyl ketones with nucleophiles: a modular entry to highly substituted furans. , 2006, Angewandte Chemie.

[21]  Chao‐Jun Li,et al.  Diastereoselective Synthesis of α‐Oxyamines via Gold‐, Silver‐ and Copper‐Catalyzed, Three‐Component Couplings of α‐Oxyaldehydes, Alkynes, and Amines in Water , 2006 .

[22]  S. Kirsch Syntheses of polysubstituted furans: recent developments. , 2006, Organic & biomolecular chemistry.

[23]  C. Che,et al.  Gold(III) Salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction. , 2006, Organic letters.

[24]  C. Che,et al.  Gold(III) porphyrin-catalyzed cycloisomerization of allenones. , 2006, Organic letters.

[25]  F. Song,et al.  Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols: highly efficient synthesis of fully substituted dihydrofurans and furans. , 2005, Organic letters.

[26]  R. Larock,et al.  Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles. , 2005, The Journal of organic chemistry.

[27]  J. Bode,et al.  Catalytic generation of activated carboxylates from enals: a product-determining role for the base. , 2005, Organic letters.

[28]  S. Kirsch,et al.  Gold(I)-catalyzed synthesis of highly substituted furans. , 2005, Organic letters.

[29]  V. Gevorgyan,et al.  1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans. , 2005, Journal of the American Chemical Society.

[30]  K. Wheeler,et al.  5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans. , 2005, Organic letters.

[31]  Richard C. D. Brown Developments in furan syntheses. , 2005, Angewandte Chemie.

[32]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[33]  R. Larock,et al.  AuCl(3)-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones. , 2004, Journal of the American Chemical Society.

[34]  A. Hashmi,et al.  Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans , 2004 .

[35]  Chao‐Jun Li,et al.  The first silver-catalyzed three-component coupling of aldehyde, alkyne, and amine. , 2003, Organic letters.

[36]  Chao‐Jun Li,et al.  A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water. , 2003, Journal of the American Chemical Society.

[37]  J. Bats,et al.  Gold catalysis: on the phenol synthesis. , 2001, Organic letters.

[38]  A. Hashmi,et al.  A New Gold-Catalyzed C—C Bond Formation. , 2000 .

[39]  Hulme,et al.  Maximizing synthetic efficiency: multi-component transformations lead the way , 2000, Chemistry.

[40]  Robert W. Armstrong,et al.  Multiple-Component Condensation Strategies for Combinatorial Library Synthesis , 1996 .

[41]  G. Posner Multicomponent one-pot annulations forming 3 to 6 bonds , 1986 .