One-pot solvent-free synthesis of quinolines by C–H activation/C–C Bond formation catalyzed by recyclable iron(III) triflate

A novel application of highly stable Fe(OTf)3 as an efficient catalyst for carbon–carbon bond formation via the activation of a terminal alkyne C–H bond under solvent-free conditions is described. Notably, this protocol of green synthesis, which produced quinolines from the reaction of amines, aldehydes and terminal aryl alkynes, shows attractive characteristics including concise one-pot conditions, high atom economy, very limited energy consumption, and the sequential catalytic process requires only a catalytic (5 mol%) amount of Fe(OTf)3 with short reaction periods (3 h). Meanwhile, the catalyst was easily recovered from the reaction system and reused smoothly with only a little loss of activity.

[1]  Changsheng Yao,et al.  Design and an efficient synthesis of natural product-based cyclopenta[b]pyran derivatives with potential bioactivity. , 2011, Bioorganic & medicinal chemistry letters.

[2]  Changsheng Yao,et al.  Design and efficient synthesis of A-278637 derivatives as potential potassium channel opener. , 2011, Bioorganic & medicinal chemistry letters.

[3]  Xiaoliang Xu,et al.  Triflic Salt–Catalyzed Coupling: Iron Triflate–Catalyzed Homocoupling of Aryl Bromides in the Presence of Metallic Magnesium , 2010 .

[4]  Changsheng Yao,et al.  One-pot combinatorial synthesis of 4-aryl-1H-thiopyrano[3,4-b]pyridine-5-one derivatives. , 2010, Journal of combinatorial chemistry.

[5]  K. Takaki,et al.  Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes. , 2010, Chemical communications.

[6]  F. Shi,et al.  Diversity synthesis of pyrimido[4,5-b][1,6]naphthyridine and its derivatives under microwave irradiation. , 2009, Journal of combinatorial chemistry.

[7]  Guigen Li,et al.  Four-component domino reaction leading to multifunctionalized quinazolines. , 2009, Journal of the American Chemical Society.

[8]  Y. Tu,et al.  Iron(III)-catalyzed and air-mediated tandem reaction of aldehydes, alkynes and amines: an efficient approach to substituted quinolines. , 2009, Chemistry.

[9]  P. Wei,et al.  New potential inhibitors of DNA topoisomerase. Part II: Design and synthesis of alpha-lapachone derivatives under microwave irradiation. , 2009, Bioorganic & medicinal chemistry letters.

[10]  Changsheng Yao,et al.  Solvent‐free synthesis of 5‐methyl‐7‐aryl‐4,7‐dihydrotetrazolo[1,5‐a]pyrimidine‐6‐carboxylic esters catalyzed by sulfamic acid , 2008 .

[11]  Changsheng Yao,et al.  One‐pot Three‐component Solvent‐free Synthesis of Benzo[4,5]imidazo[1,2‐a]pyrimidine Derivatives Catalyzed by Sulfamic Acid , 2008 .

[12]  Haijun Li,et al.  Iron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms. , 2008, Angewandte Chemie.

[13]  Fengping Xiao,et al.  Sequential catalytic process: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynes , 2008 .

[14]  Lei Shi,et al.  Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation , 2008 .

[15]  H. Adibi,et al.  Iron(III) trifluoroacetate and trifluoromethanesulfonate: Recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols , 2007 .

[16]  R. Bullock.  An iron catalyst for ketone hydrogenations under mild conditions. , 2007, Angewandte Chemie.

[17]  M. Beller,et al.  Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide. , 2007, Angewandte Chemie.

[18]  P. Walsh,et al.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions. , 2007, Chemical reviews.

[19]  William D. Kerber,et al.  H2O2 oxidations catalyzed by an iron(III) corrolazine: avoiding high-valent iron-oxido species? , 2007, Angewandte Chemie.

[20]  C. Bolm,et al.  Iron‐Catalyzed Benzylic Oxidation with Aqueous tert‐Butyl Hydroperoxide , 2007 .

[21]  M. Yus,et al.  RuCl2(dmso)4 Catalyzes the Solvent‐Free Indirect Friedländer Synthesis of Polysubstituted Quinolines from Alcohols , 2007 .

[22]  M. Beller,et al.  An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide. , 2007, Chemical communications.

[23]  C. Bolm,et al.  Iron-Catalyzed Oxidation of Cycloalkanes and Alkylarenes with Hydrogen Peroxide , 2005 .

[24]  Hasuck Kim,et al.  Efficient electrogenerated chemiluminescence from cyclometalated iridium(III) complexes. , 2005, Journal of the American Chemical Society.

[25]  P. Chirik,et al.  Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation. , 2004, Journal of the American Chemical Society.

[26]  K. Nagaiah,et al.  Silver Phosphotungstate: A Novel and Recyclable Heteropoly Acid for Friedländer Quinoline Synthesis , 2004 .

[27]  T. Kubo,et al.  Iridium-catalyzed coupling of simple primary or secondary amines, aldehydes and trimethylsilylacetylene: preparation of propargylic amines. , 2004, Chemical communications.

[28]  Y. Tu,et al.  Microwave-promoted three-component coupling of aldehyde, alkyne, and amine via C-H activation catalyzed by copper in water. , 2004, Organic letters.

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

[30]  Chao‐Jun Li,et al.  Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene. , 2002, Journal of the American Chemical Society.

[31]  Chao‐Jun Li,et al.  Highly efficient Grignard-type imine additions via C-H activation in water and under solvent-free conditions. , 2002, Chemical communications.

[32]  T. Kubo,et al.  A Three-Component Coupling Reaction of Aldehydes, Amines, and Alkynes. , 2001, Angewandte Chemie.

[33]  C. Tzeng,et al.  Synthesis and antibacterial evaluation of certain quinolone derivatives. , 2001, Journal of medicinal chemistry.

[34]  J. Michael.  Indolizidine and quinolizidine alkaloids (July 1999 to June 2000) , 2001 .

[35]  G Roma,et al.  1,8-Naphthyridines IV. 9-substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino) [1,2,4]triazolo[4,3-a][1, 8]naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities. , 2000, European journal of medicinal chemistry.

[36]  R. Sinden,et al.  Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito , 1998, Nature.

[37]  D. Boger,et al.  A Modified Friedlander Condensation for the Synthesis of 3-Hydroxyquinoline-2-carboxylates , 1995 .

[38]  S. Itoh,et al.  Synthesis and characterization of dimethyl 9,10-dihydro-9,10-dioxobenzo[f]quinoline-2,4-dicarboxylate. Effect of the pyrrole nucleus on the reactivity of coenzyme PQQ , 1992 .

[39]  Tadashi Sato,et al.  Metal-Catalyzed Organic Photoreactions. Iron(III)-Catalyzed Photoreactions of Aldo- and Ketohexoses , 1988 .

[40]  C. Moody,et al.  Synthesis of the bacterial coenzyme methoxatin , 1983 .

[41]  J. Born.  Mechanism of formation of benzo[g]quinolones via the Combes reaction , 1972 .

[42]  W. S. Johnson,et al.  Cyclization Studies in the Benzoquinoline Series , 1944 .

[43]  P. Friedländer,et al.  Ueber eine Darstellungsmethode im Pyridinkern substituirter Chinolinderivate , 1883 .