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Pure Appl. Chem., 1985, Vol. 57, No. 12, pp. 1827-1838

http://dx.doi.org/10.1351/pac198557121827

Copper-catalyzed additions of organic polyhalides to olefins: a versatile synthetic tool

D. Bellus

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  • Moustafa Gamal A. I., Suizu Hiroshi, Aoyama Hiroshi, Arai Masayoshi, Akai Shuji, Yoshimitsu Takehiko: Enantiospecific Synthesis and Cytotoxicity Evaluation of Ligudentatol: A Programmed Aromatization Approach to the 2,3,4-Trisubstituted Phenolic Motif via Visible-Light-Mediated Group Transfer Radical Cyclization. Chem. Asian J. 2014, n/a. <http://dx.doi.org/10.1002/asia.201400110>
  • Bellesia Franco, Clark Andrew J., Felluga Fulvia, Gennaro Armando, Isse Abdirisak A., Roncaglia Fabrizio, Ghelfi Franco: Efficient and Green Route to γ-Lactams by Copper-Catalysed Reversed Atom Transfer Radical Cyclisation of α-Polychloro-N -allylamides, using a Low Load of Metal (0.5 mol%). Adv. Synth. Catal. 2013, 355, 1649. <http://dx.doi.org/10.1002/adsc.201300132>
  • Nair Radhika P., Pineda-Lanorio Jocelyn A., Frost Brian J.: Atom transfer radical addition (ATRA) of carbon tetrachloride and chlorinated esters to various olefins catalyzed by Cp′Ru(PPh3)(PR3)Cl complexes. Inorganica Chimica Acta 2012, 380, 96. <http://dx.doi.org/10.1016/j.ica.2011.11.008>
  • Clark Andrew J., Collis Alana E. C., Fox David J., Halliwell Lauren L., James Natalie, O’Reilly Rachel K., Parekh Hemal, Ross Andrew, Sellars Andrew B., Willcock Helen, Wilson Paul: Atom-Transfer Cyclization with CuSO4/KBH4: A Formal “Activators Generated by Electron Transfer” Process Also Applicable to Atom-Transfer Polymerization. J. Org. Chem. 2012, 77, 6778. <http://dx.doi.org/10.1021/jo301429a>
  • Ernst Beat: Daniel Belluš (1938-2011). angew chemie 2011, 123, 11232. <http://dx.doi.org/10.1002/ange.201107084>
  • Ernst Beat: Daniel Belluš (1938-2011). Angew Chem Int E 2011, 50, 11040. <http://dx.doi.org/10.1002/anie.201107084>
  • Muñoz-Molina José María, Belderrain Tomás R., Pérez Pedro J.: Atom Transfer Radical Reactions as a Tool for Olefin Functionalization - On the Way to Practical Applications. Eur. J. Inorg. Chem. 2011, 2011, 3155. <http://dx.doi.org/10.1002/ejic.201100379>
  • Casolari Roberto, Felluga Fulvia, Frenna Vincenzo, Ghelfi Franco, Pagnoni Ugo M., Parsons Andrew F., Spinelli Domenico: A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid. Tetrahedron 2011, 67, 408. <http://dx.doi.org/10.1016/j.tet.2010.11.025>
  • Eckenhoff William T., Pintauer Tomislav: Atom transfer radical addition (ATRA) catalyzed by copper complexes with tris[2-(dimethylamino)ethyl]amine (Me6TREN) ligand in the presence of free-radical diazo initiator AIBN. Dalton Trans 2011, 40, 4909. <http://dx.doi.org/10.1039/c1dt10189g>
  • Chen Jian, Hu Chang-Ming: Addition of polyfluoropolyhaloethanes to alkenes. Chin J Chem 2010, 13, 273. <http://dx.doi.org/10.1002/cjoc.19950130313>
  • van de Kuil Lucia A., Veldhuizen Yvonne S. J., Grove David M., Zwikker Jan W., Jenneskens Leonardus W., Drenth Wiendelt, Smeets Wilberth J. J., Spek Anthony L., van Koten Gerard: Organonickel(II) complexes containing aryl ligands with chiral pyrrolidinyl ring systems; syntheses and use as homogeneous catalysts for the Kharasch addition reaction. Recl Trav Chim Pays-Bas 2010, 113, 267. <http://dx.doi.org/10.1002/recl.19941130502>
  • Weidner Karin, Giroult André, Panchaud Philippe, Renaud Philippe: Efficient Carboazidation of Alkenes Using a Radical Desulfonylative Azide Transfer Process. J Am Chem Soc 2010, 132, 17511. <http://dx.doi.org/10.1021/ja1068036>
  • Morishita Takami, Yoshida Hiroto, Ohshita Joji: Copper-catalysed bromoalkynylation of arynes. Chem Commun 2010, 46, 640. <http://dx.doi.org/10.1039/b919301d>
  • Eckenhoff William T., Pintauer Tomislav: Copper Catalyzed Atom Transfer Radical Addition (ATRA) and Cyclization (ATRC) Reactions in the Presence of Reducing Agents. Cat Rev 2010, 52, 1. <http://dx.doi.org/10.1080/01614940903238759>
  • Patten Timothy E., Olmstead Marilyn M., Troeltzsch Christina: Synthesis and characterization of an N-coordinated amidate copper(II) complex of deprotonated N-(2,6-diisopropylphenyl)-2-(bis-(2-pyridylmethyl))aminoethanamide. Inorg Chim Ada 2008, 361, 365. <http://dx.doi.org/10.1016/j.ica.2007.06.003>
  • Burg Ariela, Maimon Eric, Cohen Haim, Meyerstein Dan: Ligand Effects on the Chemical Activity of Copper(I) Complexes: Outer- and Inner-Sphere Oxidation of CuIL. Eur J Inorg Chem 2007, 2007, 530. <http://dx.doi.org/10.1002/ejic.200600702>
  • Braunecker Wade A., Matyjaszewski Krzysztof: Controlled/living radical polymerization: Features, developments, and perspectives. Prog Polym Sci 2007, 32, 93. <http://dx.doi.org/10.1016/j.progpolymsci.2006.11.002>
  • Li Hong, Zhang Yong Ming, Liu Yan Gang: Atom transfer radical polymerization of methyl methacrylate initiated with a macroinitiator of poly(vinyl acetate). J Appl Polym Sci 2006, 101, 1089. <http://dx.doi.org/10.1002/app.24002>
  • Braunecker Wade A., Matyjaszewski Krzysztof: Recent mechanistic developments in atom transfer radical polymerization. Journal of Molecular Catalysis A 2006, 254, 155. <http://dx.doi.org/10.1016/j.molcata.2006.01.076>
  • Pintauer Tomislav, Matyjaszewski Krzysztof: Structural aspects of copper catalyzed atom transfer radical polymerization. Coord Chem Rev - 2005, 249, 1155. <http://dx.doi.org/10.1016/j.ccr.2004.11.010>
  • Bellesia Franco, De Buyck Laurent, Ghelfi Franco, Pagnoni Ugo M., Strazzolini Paolo: Oxidation of Aliphatic 2,2‐Dichloroalkanals by HNO3 in CH2Cl2: An Easy and Eco‐friendly Route to the Corresponding 2,2‐Dichloroalkanoic Acids. Synth Common 2004, 34, 1473. <http://dx.doi.org/10.1081/SCC-120030698>
  • Ram, Meher Nabin Kumar: Copper(I)-Promoted Dechlorinative Surzur−Tanner Rearrangement of 2,2,2-Trichloroethyl Carboxylates. Org Lett 2003, 5, 145. <http://dx.doi.org/10.1021/ol027139u>
  • Navon Nadav, Burg Ariela, Cohen Haim, van Eldik Rudi, Meyerstein Dan: Ligand Effects on the Reactivity of CuIL Complexes Towards Cl3CCO2−. Eur J Inorg Chem 2002, 2002, 423. <http://dx.doi.org/10.1002/1099-0682(20022)2002:2<423::AID-EJIC423>3.0.CO;2-G>
  • Studer Armido: The Persistent Radical Effect in Organic Synthesis. Chem Eur J 2001, 7, 1159. <http://dx.doi.org/10.1002/1521-3765(20010316)7:6<1159::AID-CHEM1159>3.0.CO;2-I>
  • Otsu Takayuki: Iniferter concept and living radical polymerization. J Polym Sci A Polym Chem 2000, 38, 2121. <http://dx.doi.org/10.1002/(SICI)1099-0518(20000615)38:12<2121::AID-POLA10>3.0.CO;2-X>
  • Bellesia Franco, De Buyck Laurent, Ghelfi Franco, Libertini Emanuela, Pagnoni Ugo Maria, Roncaglia Fabrizio: 2,2-Dichlorination of Aldehydes with the 2,6-Lutidine·HCl/Cl2/CH2Cl2 System: an Environmentally Benign Process Suitable for Scale Up. Tetrahedron 2000, 56, 7507. <http://dx.doi.org/10.1016/S0040-4020(00)00640-2>
  • Kajiwara Atsushi, Matyjaszewski Krzysztof: EPR and Kinetic Studies of Atom Transfer Radical Polymerization of (Meth)acrylates. Polym J 1999, 31, 70. <http://dx.doi.org/10.1295/polymj.31.70>
  • Matyjaszewski Krzysztof: Transformation of “living” carbocationic and other polymerizations to controlled/“living” radical polymerization. Macromol Symp 1998, 132, 85. <http://dx.doi.org/10.1002/masy.19981320111>
  • Matyjaszewski Krzysztof: Inner sphere and outer sphere electron transfer reactions in atom transfer radical polymerization. Macromol Symp 1998, 134, 105. <http://dx.doi.org/10.1002/masy.19981340112>
  • Metzger Jürgen O., Mahler Ralf, Francke Gerald: Radical Additions of Alkyl 2-Haloalkanoates and 2-Haloalkanenitriles to Alkenes Initiated by Electron Transfer from Copper in Solvent-Free Systems. Liebigs Ann /Recueil 1997, 1997, 2303. <http://dx.doi.org/10.1002/jlac.199719971119>
  • Forti Luca, Ghelfi Franco, Pagnoni Ugo M.: Ferrocene promoted addition of methyl 2,2-dichloro-carboxylates to 1-alkenes. Tetrahedron 1997, 53, 4419. <http://dx.doi.org/10.1016/S0040-4020(97)00112-9>
  • Bellesia Franco, Forti Luca, Ghelfi Franco, Pagnoni Ugo M.: The Fe0 Promoted Addition of CCI4, and CCI3Br to Olefins. Synth Common 1997, 27, 961. <http://dx.doi.org/10.1080/00397919708003040>
  • Matyjaszewski Krzysztof: Controlled radical polymerization. Current Opinion Solid State Mater Sci 1996, 1, 769. <http://dx.doi.org/10.1016/S1359-0286(96)80101-X>
  • Forti Luca, Ghelfi Franco, Lancellotti Massimiliano Lodi, Pagnoni Ugo M.: The CuBr/Fe0 Promoted Radical Addition of Methyl 2-Br-2-Cl-Carboxylates to OLEFINS. Synth Common 1996, 26, 1699. <http://dx.doi.org/10.1080/00397919608002609>
  • Metzger Jügen O., Mahler Ralf: Lösungsmittelfreie, durch Elektronenübertragung von Kupfer initiierte radikalische Additionen von aktivierten Halogenalkanen an Alkene. Angew Chem 1995, 107, 1012. <http://dx.doi.org/10.1002/ange.19951070827>
  • Shvekhgeimer G. A.: Synthesis of pyridine derivatives. Intramolecular cyclization of δ-oxonitriles (Review). Chem Heterocycl Compd 1995, 31, 651. <http://dx.doi.org/10.1007/BF01169066>
  • Dowd Paul, Zhang Wei, Mahmood Khalid: Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones. Tetrahedron 1995, 51, 39. <http://dx.doi.org/10.1016/0040-4020(94)00961-S>
  • Dowd Paul, Zhang Wei, Geib Steven J.: Free radical annulation of dichlorocyclobutanones with sequential ring expansion. Tetrahedron 1995, 51, 3435. <http://dx.doi.org/10.1016/0040-4020(95)00093-N>
  • Benincasa Marta, Forti Luca, Ghelfi Franco, Pagnoni Ugo M.: Reductive homo-coupling of methyl 2-Br-2-Cl-carboxylates promoted by CuBrFe0. Tetrahetron Lett 1995, 36, 1103. <http://dx.doi.org/10.1016/0040-4039(94)02405-Z>
  • Pirrung Frank O.H., Hiemstra Henk, Nico Speckamp W., Kaptein Bernard, Schoemaker Hans E.: Synthesis of medium-sized lactones by the copper(I)chloride/2,2′-bipyridine-catalyzed cyclization of di- and trichloroacetates. Tetrahedron 1994, 50, 12415. <http://dx.doi.org/10.1016/S0040-4020(01)89549-1>
  • Sugimoto Kikuo, Sakai Kunikazu, Shigeizumi Sanae, Kondo Kiyosi: A new selective dichlorination of CC double bonds. Tetrahetron Lett 1994, 35, 737. <http://dx.doi.org/10.1016/S0040-4039(00)75804-7>
  • Zhang Wie, Dowd Paul: Stereospecific annulation and sequential ring-opening of (R)-carvone: Formation of a novel tricyclic dione. Tetrahetron Lett 1994, 35, 5161. <http://dx.doi.org/10.1016/S0040-4039(00)77053-5>
  • Dowd Paul, Zhang Wei, Mahmood Khalid: A cyclobutanone-based tandem free radical rearrangement. Tetrahetron Lett 1994, 35, 5563. <http://dx.doi.org/10.1016/S0040-4039(00)77247-9>
  • Vionnet Jean-Paul, Schenk Kurt, Renaud Philippe: Regioselective Radical Additions to 7-Oxabicyclo[2.2.1]hept-5-en-2-one. HCA 1993, 76, 2490. <http://dx.doi.org/10.1002/hlca.19930760708>
  • Seijas Julio A., Vázquez-Tato M.Pilar, Castedo Luis, Estévez Ramón J., Ónega M.Gabriela, Ruíz Maria: Synthesis of pyrrolizidines via copper(I) catalyzed radical atom transfer cyclization. Tetrahedron 1992, 48, 1637. <http://dx.doi.org/10.1016/S0040-4020(01)88722-6>
  • Sieburth Scott McN., Ali Syed F., Langevine Charles M., Tullman Robert H.: Stereoselective synthesis of hydroxylated bifenthrin isomers. Biorg Med Chem Lett 1992, 2, 1585. <http://dx.doi.org/10.1016/S0960-894X(00)80435-7>
  • Udding Jan H., Hiemstra Henk, van Zanden Marco N.A., Speckamp W.Nico: Copper catalyzed chlorine transfer cyclizations of glycine and glycolic acid derivatives. Tetrahetron Lett 1991, 32, 3123. <http://dx.doi.org/10.1016/0040-4039(91)80706-C>
  • Curran Dennis P., Chang Chi-Tai: Evidence that palladium(0)-promoted cyclizations of unsaturated α-iodocarbonyls occur by an atom transfer mechanism. Tetrahetron Lett 1990, 31, 933. <http://dx.doi.org/10.1016/S0040-4039(00)94396-X>
  • Grove David M., Verschuuren Augustinus H.M., van Koten Gerard, van Beek Johannes A.M.: The homogeneously catalysed addition reaction of polyhalogenoalkanes to olefins by divalent arylnickel complexes: comparative reactivity and some important mechanistic leads. J Organomet Chem 1989, 372, C1. <http://dx.doi.org/10.1016/0022-328X(89)87088-3>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1986. J Organomet Chem 1988, 343, 147. <http://dx.doi.org/10.1016/0022-328X(88)80176-1>
  • Grove David M., Van Koten Gerard, Verschuuren Augustinus H.M.: New Homogeneous Catalysts in the Addition of Polyhalogenoalkanes to Olefins; Organonickel(II) Complexes [Ni{C6H3(CH2NMe2)2-o,o'}X] (X = Cl, Br, I). Journal of Molecular Catalysis 1988, 45, 169. <http://dx.doi.org/10.1016/0304-5102(88)80006-3>
  • Fujita Makoto, Hiyama Tamejiro: Practical ways from aldehydes to 2-chloro-1,1,1-trifluoro-2-alkenes and 2-chloro-1,1-difluoro-1-alken-3-ols. Tetrahetron Lett 1986, 27, 3655. <http://dx.doi.org/10.1016/S0040-4039(00)84873-X>