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Pure Appl. Chem., 1996, Vol. 68, No. 1, pp. 53-60

http://dx.doi.org/10.1351/pac199668010053

Cu-catalyzed alkylation and Fe catalyzed alkenylation of organomanganese reagents

Gérard Cahiez and Sophie Marquais

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  • Sun Chang-Liang, Krause Helga, Fürstner Alois: A Practical Procedure for Iron-Catalyzed Cross-Coupling Reactions of Sterically Hindered Aryl-Grignard Reagents with Primary Alkyl Halides. Adv. Synth. Catal. 2014, 356, 1281. <http://dx.doi.org/10.1002/adsc.201301089>
  • Denmark Scott E., Cresswell Alexander J.: Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents. J. Org. Chem. 2013, 78, 12593. <http://dx.doi.org/10.1021/jo402246h>
  • Cahiez Gérard, Gager Olivier, Moyeux Alban, Delacroix Thomas: Efficient Procedures to Prepare Primary and Secondary Alkyl Halides from Alkanols via the Corresponding Sulfonates under Mild Conditions. Adv. Synth. Catal. 2012, 354, 1519. <http://dx.doi.org/10.1002/adsc.201100736>
  • dos Santos Marcelo R., Diniz Julia R., Arouca Aline M., Gomes Alexandre F., Gozzo Fabio C., Tamborim Silvia M., Parize Alexandre L., Suarez Paulo A. Z., Neto Brenno A. D.: Ionically Tagged Iron Complex-Catalyzed Epoxidation of Olefins in Imidazolium-Based Ionic Liquids. ChemSusChem 2012, 5, 716. <http://dx.doi.org/10.1002/cssc.201100453>
  • Santos Marcelo R. dos, Gomes Alexandre F., Gozzo Fabio C., Suarez Paulo A. Z., Neto Brenno A. D.: Iron Complex with Ionic Tag-Catalyzed Olefin Reduction under Oxidative Conditions-A Different Reaction for Iron. ChemSusChem 2012, 5, 2383. <http://dx.doi.org/10.1002/cssc.201200344>
  • Li Bin, Liu An-Hua, He Liang-Nian, Yang Zhen-Zhen, Gao Jian, Chen Kai-Hong: Iron-catalyzed selective oxidation of sulfides to sulfoxides with the polyethylene glycol/O2 system. Green Chem 2012, 14, 130. <http://dx.doi.org/10.1039/c1gc15821j>
  • Ito Shingo, Itoh Takuma, Nakamura Masaharu: Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis. Angew Chem 2011, 123, 474. <http://dx.doi.org/10.1002/ange.201006180>
  • Ito Shingo, Itoh Takuma, Nakamura Masaharu: Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis. Angew Chem Int Ed 2011, 50, 454. <http://dx.doi.org/10.1002/anie.201006180>
  • Weber Katharina, Schnöckelborg Eva-Maria, Wolf Robert: Catalytic Properties of Low Oxidation State Iron Complexes in Cross-Coupling Reactions: Anthracene Iron(−I) Complexes as Competent Catalysts. ChemCatChem 2011, 3, 1572. <http://dx.doi.org/10.1002/cctc.201100199>
  • Gowda Ravikumar R., Chakraborty Debashis: FeIII-Catalyzed Synthesis of Primary Amides from Aldehydes. Eur J Org Chem 2011, 2011, 2226. <http://dx.doi.org/10.1002/ejoc.201001738>
  • Xu Guoqiang, Li Xiaoyan, Sun Hongjian: Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents. J Organomet Chem 2011, 696, 3011. <http://dx.doi.org/10.1016/j.jorganchem.2011.05.017>
  • Kutubi Md. Shahajahan, Kitamura Tsugio: Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles. Tetrahed 2011, 67, 8140. <http://dx.doi.org/10.1016/j.tet.2011.08.051>
  • Reddy M. Amarnath, Reddy P. Surendra, Sreedhar B.: Iron(III) Chloride-Catalyzed Direct Sulfonylation of Alcohols with Sodium Arenesulfinates. Adv Synth Catal 2010, 352, 1861. <http://dx.doi.org/10.1002/adsc.200900905>
  • Cahiez Gérard, Gager Olivier, Buendia Julien: Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides. Angew Chem 2010, 122, 1300. <http://dx.doi.org/10.1002/ange.200905816>
  • Cahiez Gérard, Gager Olivier, Buendia Julien: Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides. Angew Chem Int Ed 2010, 49, 1278. <http://dx.doi.org/10.1002/anie.200905816>
  • Biswas Srijit, Maiti Sukhendu, Jana Umasish: An Efficient Iron-Catalyzed Carbon-Carbon Single-Bond Cleavage via Retro-Claisen Condensation: A Mild and Convenient Approach to Synthesize a Variety of Esters or Ketones. Eur J Org Chem 2010, 2010, 2861. <http://dx.doi.org/10.1002/ejoc.201000128>
  • Castagnolo Daniele, Botta Maurizio: Iron-Catalyzed Cross-Coupling between 1-Bromoalkynes and Grignard-Derived Organocuprate Reagents. Eur J Org 2010, 2010, 3224. <http://dx.doi.org/10.1002/ejoc.201000393>
  • Bézier David, Darcel Christophe: Retraction: Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction. Adv Synth Catal 2009, 351, 1732. <http://dx.doi.org/10.1002/adsc.200900281>
  • Cahiez Gérard, Foulgoc Laura, Moyeux Alban: Iron-Catalyzed Oxidative Heterocoupling Between Aliphatic and Aromatic Organozinc Reagents: A Novel Pathway for Functionalized Aryl-Alkyl Cross-Coupling Reactions. Angew. Chem. 2009, 121, 3013. <http://dx.doi.org/10.1002/ange.200900175>
  • Cahiez Gérard, Duplais Christophe, Buendia Julien: Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant. Angew Chem 2009, 121, 6859. <http://dx.doi.org/10.1002/ange.200902188>
  • Cahiez Gérard, Foulgoc Laura, Moyeux Alban: Iron-Catalyzed Oxidative Heterocoupling Between Aliphatic and Aromatic Organozinc Reagents: A Novel Pathway for Functionalized Aryl-Alkyl Cross-Coupling Reactions. Angew Chem Int Ed 2009, 48, 2969. <http://dx.doi.org/10.1002/anie.200900175>
  • Cahiez Gérard, Duplais Christophe, Buendia Julien: Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant. Angew Chem Int Ed 2009, 48, 6731. <http://dx.doi.org/10.1002/anie.200902188>
  • Kleimark Jonatan, Hedström Anna, Larsson Per-Fredrik, Johansson Charlotte, Norrby Per-Ola: Mechanistic Investigation of Iron-Catalyzed Coupling Reactions. ChemCatChem 2009, 1, 152. <http://dx.doi.org/10.1002/cctc.200900061>
  • Czaplik Waldemar Maximilian, Mayer Matthias, Cvengroš Ján, von Wangelin Axel Jacobi: Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions. ChemSusChem 2009, 2, 396. <http://dx.doi.org/10.1002/cssc.200900055>
  • Wu Xiao-Feng, Vovard-Le Bray Chloé, Bechki Lazhar, Darcel Christophe: Iron-catalyzed sulfonylimine synthesis under neutral conditions. Tetrahedron 2009, 65, 7380. <http://dx.doi.org/10.1016/j.tet.2009.07.029>
  • Poizot Philippe, Jouikov Viatcheslav, Simonet Jacques: Glassy carbon modified by a silver–palladium alloy: cheap and convenient cathodes for the selective reductive homocoupling of alkyl iodides. Tetrahetron Lett 2009, 50, 822. <http://dx.doi.org/10.1016/j.tetlet.2008.12.008>
  • Dongol Krishna G., Koh Huishi, Sau Manisankar, Chai Christina L. L.: Iron-Catalysedsp3–sp3 Cross-Coupling Reactions of Unactivated Alkyl Halides with Alkyl Grignard Reagents. Adv Synth Catal 2007, 349, 1015. <http://dx.doi.org/10.1002/adsc.200600383>
  • Kofink Christiane C., Blank Beno?t, Pagano Sandro, G?tz Nadine, Knochel Paul: Iron-catalyzed aryl?aryl cross-coupling reaction tolerating amides and unprotected quinolinones. Chem Commun 2007, 1954. <http://dx.doi.org/10.1039/b618617c>
  • Ila Hiriyakkanavar, Baron Oliver, Wagner Andreas J., Knochel Paul: Functionalized magnesium organometallics as versatile intermediates for the synthesis of polyfunctional heterocycles. Chem Commun 2006, 583. <http://dx.doi.org/10.1039/b510866g>
  • Sapountzis Ioannis, Lin Wenwei, Kofink Christiane C., Despotopoulou Christina, Knochel Paul: Eisenkatalysierte Aryl-Aryl-Kreuzkupplungen mit Kupferreagentien. Angew Chem 2005, 117, 1682. <http://dx.doi.org/10.1002/ange.200462013>
  • Korn Tobias J., Knochel Paul: Cobalt(II)-katalysierte Kreuzkupplungen von Arylkupferreagentien mit Arylbromiden oder -chloriden. Angew Chem 2005, 117, 3007. <http://dx.doi.org/10.1002/ange.200500099>
  • Sapountzis Ioannis, Lin Wenwei, Kofink Christiane C., Despotopoulou Christina, Knochel Paul: Iron-Catalyzed Aryl-Aryl Cross-Couplings with Magnesium-Derived Copper Reagents. Angew Chem Int Ed 2005, 44, 1654. <http://dx.doi.org/10.1002/anie.200462013>
  • Korn Tobias J., Knochel Paul: Cobalt(II)-Catalyzed Cross-Coupling of Polyfunctional Aryl Copper Reagents with Aryl Bromides and Chlorides. Angew Chem Int Ed 2005, 44, 2947. <http://dx.doi.org/10.1002/anie.200500099>
  • Fürstner Alois, Martin Rubén: Advances in Iron Catalyzed Cross Coupling Reactions. Chem Lett 2005, 34, 624. <http://dx.doi.org/10.1246/cl.2005.624>
  • Ohmiya Hirohisa, Tsuji Takashi, Yorimitsu Hideki, Oshima Koichiro: Cobalt-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Allylic and Benzylic Grignard Reagents and Their Application to Tandem Radical Cyclization/Cross-Coupling Reactions. Chem Eur J 2004, 10, 5640. <http://dx.doi.org/10.1002/chem.200400545>
  • Nagano Takashi, Hayashi Tamio: Iron-Catalyzed Grignard Cross-Coupling with Alkyl Halides Possessing β-Hydrogens. Org Lett 2004, 6, 1297. <http://dx.doi.org/10.1021/ol049779y>
  • Vu Viet Anh, Knochel Paul, Dohle Wolfgang, Gommermann Nina, Kneisel Florian F., Kopp Felix, Korn Tobias, Sapountzis Ioannis: Highly Functionalized Organomagnesium Reagents Prepared through Halogen-Metal Exchange. Angew Chem Int Ed 2003, 42, 4302. <http://dx.doi.org/10.1002/anie.200300579>
  • Tang Jun, Shinokubo Hiroshi, Oshima Koichiro: A new strategy for the preparation of an active Mn(0) and its use for radical cyclization reactions. Tetrahedron 1999, 55, 1893. <http://dx.doi.org/10.1016/S0040-4020(98)01205-8>
  • Cahiez Gérard, Martin Arnaud, Delacroix Thomas: A new convenient procedure to prepare organomanganese reagents from organic halides and activated manganese. Tetrahetron Lett 1999, 40, 6407. <http://dx.doi.org/10.1016/S0040-4039(99)01331-3>
  • Cahiez Gérard, Avedissian Hovsep: Cobalt-catalyzed alkenylation of organomagnesium reagents. Tetrahetron Lett 1998, 39, 6159. <http://dx.doi.org/10.1016/S0040-4039(98)01266-0>
  • Kim Seung-Hoi, Rieke Reuben D.: Direct Preparation of Arylmanganese Bromides Using Active Manganese. Synth Common 1998, 28, 1065. <http://dx.doi.org/10.1080/00397919808003074>
  • Klement Ingo, Stadtmüller Heinz, Knochel Paul, Cahiez Gérard: Preparation and reactivity of functionalized aryl and alkenylmanganese halides. Tetrahetron Lett 1997, 38, 1927. <http://dx.doi.org/10.1016/S0040-4039(97)00248-7>
  • Riguet Eric, Alami Mouâd, Cahiez Gérard: Palladium-catalyzed selective synthesis of unsymmetrical biaryls from aryl halides or triflates and organomanganese reagents. Tetrahetron Lett 1997, 38, 4397. <http://dx.doi.org/10.1016/S0040-4039(97)00940-4>
  • Reddy C. Kishan, Knochel Paul: Neue Cobalt- und Eisen-katalysierte Reaktionen mit Organozinkverbindungen. Angew Chem 1996, 108, 1812. <http://dx.doi.org/10.1002/ange.19961081523>
  • Fürstner Alois, Brunner Heiko: Preparation of allyl-, alkenyl- and of functionalized arylmanganese reagents by oxidative insertion of manganese-graphite into organic halides. Tetrahetron Lett 1996, 37, 7009. <http://dx.doi.org/10.1016/0040-4039(96)01591-2>