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Pure Appl. Chem., 1987, Vol. 59, No. 8, pp. 937-946

Bismuth(V) reagents in organic synthesis

D. H. R. Barton and J.-P. Finet

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  • Crifar Cynthia, Petiot Pauline, Ahmad Tabinda, Gagnon Alexandre: Synthesis of Highly Functionalized Diaryl Ethers by Copper-Mediated O-Arylation of Phenols using Trivalent Arylbismuth Reagents. Chem. Eur. J. 2014, 20, 2755. <>
  • Wang Tao, Sang Shuai, Liu Liu, Qiao Hongwei, Gao Yuxing, Zhao Yufen: Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds. J. Org. Chem. 2014, 79, 608. <>
  • Gagnon Alexandre, Petiot Pauline: Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuthines with 2-Haloazines and Diazines. HETEROCYCLES 2014, 88, 1615. <>
  • Goswami Manibarsha, Ellern Arkady, Pohl Nicola L. B.: Bismuth(V)-Mediated Thioglycoside Activation. Angew. Chem. 2013, 125, 8599. <>
  • Goswami Manibarsha, Ellern Arkady, Pohl Nicola L. B.: Bismuth(V)-Mediated Thioglycoside Activation. Angew. Chem. Int. Ed. 2013, 52, 8441. <>
  • Benaskar Faysal, Patil Narendra G., Rebrov Evgeny V., Ben-Abdelmoumen Alladin, Meuldijk Jan, Hulshof Lumbertus A., Hessel Volker, Schouten Jaap C.: Micro/Milliflow Processing with Selective Catalyst Microwave Heating in the Cu-Catalyzed Ullmann Etherification Reaction: A μ2 -Process. ChemSusChem 2013, 6, 353. <>
  • Petiot Pauline, Gagnon Alexandre: Palladium-Catalyzed Cross-Coupling Reaction of Functionalized Aryl- and Hetero­arylbismuthanes with 2-Halo(or 2-Triflyl)­azines and -diazines. Eur. J. Org. Chem. 2013, 2013, 5282. <>
  • Huang Xueliang, Patil Mahendra, Farès Christophe, Thiel Walter, Maulide Nuno: Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds. J. Am. Chem. Soc. 2013, 135, 7312. <>
  • Xu Qing-Long, Gao Hongyin, Yousufuddin Muhammed, Ess Daniel H., Kürti László: Aerobic, Transition-Metal-Free, Direct, and Regiospecific Mono-α-arylation of Ketones: Synthesis and Mechanism by DFT Calculations. J. Am. Chem. Soc. 2013, 135, 14048. <>
  • Benaskar Faysal, Engels Volker, Rebrov Evgeny V., Patil Narendra G., Meuldijk Jan, Thüne Peter C., Magusin Pieter C. M. M., Mezari Brahim, Hessel Volker, Hulshof Lumbertus A.: New Cu-Based Catalysts Supported on TiO2 Films for Ullmann SNAr-Type CO Coupling Reactions. Chemistry A European Journal 2012, 18, 1800. <>
  • Salvador Jorge AR, Figueiredo Sandra AC, Pinto Rui MA, Silvestre Samuel M: Bismuth compounds in medicinal chemistry. Future Medicinal Chemistry 2012, 4, 1495. <>
  • Valerio Viviana, Madelaine Claire, Maulide Nuno: Steering Reaction Pathways: From Benzyl Claisen Rearrangements to Powerful Ionic Shifts. Chemistry A European Journal 2011, 17, 4742. <>
  • Huang Xueliang, Maulide Nuno: Sulfoxide-Mediated α-Arylation of Carbonyl Compounds. J Am Chem Soc 2011, 133, 8510. <>
  • Sueda Takuya, Oshima Ayumi, Teno Naoki: N-Alkynyl Imides (Ynimides): Synthesis and Use as a Variant of Highly Labile Ethynamine. Org Lett 2011, 13, 3996. <>
  • Riaño S., Fernández D., Fadini L.: Oxidative cleavage of vic-diols catalyzed by manganese (III) complexes in ionic liquids. Catal Commun 2008, 9, 1282. <>
  • Sakurai Naoto, Mukaiyama Teruaki: Direct α-Oxytosylation of Ketones by Using Pentavalent Organobismuth Reagents. Chem Lett 2008, 37, 388. <>
  • Sakurai Naoto, Mukaiyama Teruaki: New Preparative Method of Aryl Tosylates by Using Organobismuth Reagents. Chem Lett 2007, 36, 928. <>
  • Mukaiyama Teruaki, Sakurai Naoto: A New Preparative Method of Aryl Sulfonate Esters by Using Cyclic Organobismuth Reagents. HETEROCYCLES 2007, 74, 771. <>
  • Finet Jean-Pierre, Fedorov Alexey Yu.: Tris(polymethoxyphenyl)bismuth derivatives: Synthesis and reactivity. J Organomet Chem 2006, 691, 2386. <>
  • Koech Phillip K., Krische Michael J.: Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation. Tetrahedron 2006, 62, 10594. <>
  • Répichet Sigrid, Le Roux Christophe, Roques Nicolas, Dubac Jacques: BiCl3-catalyzed Friedel–Crafts acylation reactions: bismuth(III) oxychloride as a water insensitive and recyclable procatalyst. Tetrahetron Lett 2003, 44, 2037. <>
  • Ménard Cécilia, Doris Eric, Mioskowski Charles: Ph3BiCO3: a mild reagent for in situ oxidation of urazoles to triazolinediones. Tetrahetron Lett 2003, 44, 6591. <>
  • Oxidizing Ability of a Series of (Tropon-2-ylimino)pnictoranes (Pnictogen = P, As, Sb, and Bi) toward Some Alcohols. Bull Chem Soc Jpn 2003, 76, 1029. <>
  • Yue Wen Song, Li Jie Jack: A Concise Synthesis of All Four Possible Benzo[4,5]furopyridines via Palladium-Mediated Reactions. Org Lett 2002, 4, 2201. <>
  • Elliott Gregory I., Konopelski Joseph P.: Arylation with organolead and organobismuth reagents. Tetrahedron 2001, 57, 5683. <>
  • Kirij N.V., Pasenok S.V., Yagupolskii Yu.L., Tyrra W., Naumann D.: Bi(CF3)3/Cu(OCOCH3)2 — a new system for the synthesis of 2-trifluoromethylcycloalkan-1-ones, trifluoromethylanilines and phenyl(trifluoromethyl)sulfane. J FLUORINE CHEM 2000, 106, 217. <>
  • Combes Sbastien, Finet Jean-Pierre: On the exclusion of radical species in the ligand coupling reactions with pentavalent triarylbismuth derivatives. Tetrahedron 1999, 55, 3377. <>
  • Ohe Toshiyuki, Tanaka Takumi, Kuroda Masashi, Cho Chan Sik, Ohe Kouichi, Uemura Sakae: Palladium(II)-Catalyzed Aryl Coupling of Triarylbismuthines under Air. Bull Chem Soc Jpn 1999, 72, 1851. <>
  • Combes Sébastien, Finet Jean-Pierre: Triarylbismuthane - iodobenzene diacetate: One-pot system for copper-catalysed N-arylation under neutral conditions. Tetrahedron 1998, 54, 4313. <>
  • Banik Bimal K., Venkatraman M.S., Mukhopadhyay Chhanda, Becker Frederick F.: Benzylic oxidation by sodium bismuthate in acetic acid: A simple method for the synthesis of polycyclic aromatic ketones. Tetrahetron Lett 1998, 39, 7247. <>
  • Arnauld Thomas, Barton Derek H.R., Doris Eric: The chemistry of pentavalent organobismuth reagents. New preparative methods for aryl bismuth (V) carboxylates and sulfonates. Tetrahetron Lett 1997, 38, 365. <>
  • Shen Zhen, Zhang Jinqi, Zou Huixian, Yang Minmin: A novel one-pot reformatsky type reaction via bismuth salt in aqueous media. Tetrahetron Lett 1997, 38, 2733. <>
  • Wada Makoto, Takahashi Toshikazu, Domae Terutomo, Fukuma Tomohiro, Miyoshi Norikazu, Smith Keith: Asymmetric trimethylsilylcyanation of aldehydes utilizing chiral bismuth compounds. A frontier in bismuth mediated synthetic reactions. Tet Asymm 1997, 8, 3939. <>
  • Postel M., Duñach E.: Bismuth derivatives for the oxidation of organic compounds. Coord Chem Rev - 1996, 155, 127. <>
  • Barton Derek H.R., Doris Eric: Alkylation of aromatic amines and related compounds using a copper(II)-aluminum(III) couple. Tetrahetron Lett 1996, 37, 3295. <>
  • Sinclair Peter J., Wong Frederick, Staruch Mary Jo, Wiederrecht Greg, Parsons William H., Dumont Francis, Wyvratt Mathew: Preparation and in vitro activities of naphthyl and indolyl ether derivatives of the FK-506 related immunosuppressive macrolide ascomycin. Biorg Med Chem Lett 1996, 6, 2193. <>
  • Combes Sébastien, Finet Jean-Pierre: A Convenient Synthesis of Triarylbismuth Diacetates. Synth Common 1996, 26, 4569. <>
  • Matano Yoshihiro, Suzuki Hitomi: A New Aspect of Organobismuth Chemistry: Synthesis, Properties, and Reactions of Bismuthonium Compounds. Bull Chem Soc Jpn 1996, 69, 2673. <>
  • Sinclair Peter J., Wong Frederick, Wyvratt Matthew, Staruch Mary Jo, Dumont Francis: Preparation and in vitro activity of aryl ether derivatives of the FK-506 related immunosuppressive macrolides ascomycin and L-683,742. Biorg Med Chem Lett 1995, 5, 1035. <>
  • Cho Chan Sik, Yoshimori Yasuharu, Uemura Sakae: Rhodium(I)- and Palladium(0)-Catalyzed Carbonylation of Triarylbismuthines with Carbon Monoxide via a Possible Oxidative Addition of a Carbon-Bismuth Bond to Rhodium(I) and Palladium(0). Bull Chem Soc Jpn 1995, 68, 950. <>
  • Goulet Mark T., Rupprecht Kathleen M., Sinclair Peter J., Wyvratt Matthew J., Parsons William H.: The medicinal chemistry of FK-506. PERSPECT DRUG DISCOV DES 1994, 2, 145. <>
  • Borah Harsha N., Prajapati Dipak, Sandhu Jagir S., Ghosh Anil C.: Bismuth(III) chloride-zinc promoted selective reduction of aromatic nitro compounds to azoxy compounds. Tetrahetron Lett 1994, 35, 3167. <>
  • Whitmire Kenton H., Labahn D., Roesky Herbert W., Noltemeyer Matthias, Sheldrick George M.: Sterically crowded aryl bismuth compounds: synthesis and characterization of bis{2,4,6-tris(trifluoromethyl)phenyl} bismuth chloride and tris{2,4,6-tris(trifluoromethyl)phenyl} bismuth. J Organomet Chem 1991, 402, 55. <>
  • Whitmire Kenton H., Roesky Herbert W., Brooker Sally, Sheldrick George M.: CF bond activation in the reaction of BiCl3 with sodium 2,4,6-tris(trifluoromethyl)phenoxide. J Organomet Chem 1991, 402, C4. <>
  • Wakabayashi S., Kiyohara Y., Kameda S., Uenishi J., Oae S.: Ligand coupling of 2-pyridyl sulfoxides having an sp2 stereocenter at the α-position: A novel preparation of α-stilbazoles. Heteroatom Chem 1990, 1, 225. <>
  • Doak G.O., Freedman Leon D.: Bismuth Annual survey covering the year 1987. J Organomet Chem 1989, 360, 297. <>
  • Barton Derek H.R, Finet Jean-Pierre, Khamsi Jamal: N-phenylation of amino acid derivatives. Tetrahetron Lett 1989, 30, 937. <>
  • Barton Derek H.R., Ozbalik Nubar, Ramesh Manian: Tetrahedron 1988, 44, 5661. <>
  • Barton Derek H.R., Donnelly Dervilla M.X., Finet Jean-Pierre, Stenson Paul H.: The chemistry of pentavalent organobismuth reagents. Tetrahedron 1988, 44, 6387. <>
  • Ohki Hidenori, Wada Makoto, Akiba Kin-ya: Bismuth trichloride as a new efficient catalyst in the aldol reaction. Tetrahetron Lett 1988, 29, 4719. <>
  • Akiba Kin-ya, Ohdoi Keisuke, Yamamoto Yohsuke: Synthesis and halogenolysis of stable pentacoordinate bismuthcompounds (10-Bi-5): formation of1-chloro-1,1-diaryl-3,3-bis(trifluoromethyl)-3H-2,1-benzoxabismoles. Tetrahetron Lett 1988, 29, 3817. <>
  • Schmuck Arno, Buschmann Jürgen, Fuchs Joachim, Seppelt Konrad: Struktur und Farbe von Pentaphenylbismut. Angew Chem 1987, 99, 1206. <>