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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 209-214

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

Lutz Ackermann, Robert Born, Julia H. Spatz, Andreas Althammer and Christian J. Gschrei

Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5-13, Haus F, 81377 München, Germany

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  • Sun Alex D., Leung Kaylyn, Restivo Anita D., LaBerge Nicole A., Takasaki Harumi, Love Jennifer A.: Nickel-Catalyzed Csp2 Csp3 Bond Formation by CarbonFluorine Activation. Chem. Eur. J. 2014, 20, 3162. <>
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  • Martin Carmen, Mallet-Ladeira Sonia, Miqueu Karinne, Bouhadir Ghenwa, Bourissou Didier: Combined Experimental/Computational Study of Iridium and Palladium Hydride PP(O)P Pincer Complexes. Organometallics 2014, 33, 571. <>
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  • Clavier Hervé, Lepronier Aymeric, Bengobesse-Mintsa Nathalie, Gatineau David, Pellissier Hélène, Giordano Laurent, Tenaglia Alphonse, Buono Gérard: Palladium-Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides. Adv. Synth. Catal. 2013, n/a. <>
  • Donets Pavel A., Cramer Nicolai: Diaminophosphine Oxide Ligand Enabled Asymmetric Nickel-Catalyzed Hydrocarbamoylations of Alkenes. J. Am. Chem. Soc. 2013, 135, 11772. <>
  • Guo Wang-Jun, Wang Zhong-Xia: Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel Complexes. J. Org. Chem. 2013, 78, 1054. <>
  • Rafter Eoin, Gutmann Torsten, Löw Florian, Buntkowsky Gerd, Philippot Karine, Chaudret Bruno, van Leeuwen Piet W. N. M.: Secondary phosphine oxides as pre-ligands for nanoparticle stabilization. Catal. Sci. Technol. 2013, 3, 595. <>
  • Shan Gang, Han Xuesong, Lin Yun, Yu Shanyou, Rao Yu: Broadening the catalyst and reaction scope of regio- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis. Org. Biomol. Chem. 2013, 11, 2318. <>
  • Veerashekhar Goud E., Pavan Kumar B.B., Shruthi Yacham, Paul Arijitha, Sivaramakrishna Akella, Vijayakrishna Kari, Brahmananda Rao C.V.S., Sabharwal K.N., Clayton H.S.: Investigations on synthesis, thermolysis, and coordination chemistry of aminophosphine oxides. Journal of Coordination Chemistry 2013, 66, 2647. <>
  • Jin Zhong, Li Yan-Jing, Ma Yong-Qiang, Qiu Ling-Ling, Fang Jian-Xin: Biphenyl-Based Diaminophosphine Oxides as Air-Stable Preligands for the Nickel-Catalyzed Kumada-Tamao-Corriu Coupling of Deactivated Aryl Chlorides, Fluorides, and Tosylates. Chemistry A European Journal 2012, 18, 446. <>
  • Kuehnel Moritz F., Holstein Philipp, Kliche Meike, Krüger Juliane, Matthies Stefan, Nitsch Dominik, Schutt Joseph, Sparenberg Michael, Lentz Dieter: Titanium-Catalyzed Vinylic and Allylic CF Bond Activation-Scope, Limitations and Mechanistic Insight. Chem. Eur. J. 2012, 18, 10701. <>
  • Shaikh Tanveer Mahamadali, Weng Chia-Ming, Hong Fung-E, Curtis Neil F.: Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions. Coordination Chemistry Reviews 2012, 256, 771. <>
  • Ackermann Lutz, Diers Emelyne, Manvar Atul: Ruthenium-Catalyzed C–H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles. Org Lett 2012, 14, 1154. <>
  • Ackermann Lutz, Kornhaass Christoph, Zhu Yingjun: Palladium-Catalyzed Direct C–H Bond Alkynylations of Heteroarenes Using gem-Dichloroalkenes. Z Org Lett 2012, 14, 1824. <>
  • Yang Yiqing, Lin Yun, Rao Yu: Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group. Org. Lett. 2012, 120522105335003. <>
  • Gusarova Nina K., Arbuzova Svetlana N., Trofimov Boris A.: Novel general halogen-free methodology for the synthesis of organophosphorus compounds. PureAppl Chem 2012, 1. <>
  • Ackermann Lutz, Punji Benudhar, Song Weifeng: User-Friendly [(Diglyme)NiBr2]-Catalyzed Direct Alkylations of Heteroarenes with Unactivated Alkyl Halides through CH Bond Cleavages. Synth Catal 2011, 353, 3325. <>
  • Achard Thierry, Lepronier Aymeric, Gimbert Yves, Clavier Hervé, Giordano Laurent, Tenaglia Alphonse, Buono Gérard: A Regio- and Diastereoselective Platinum-Catalyzed Tandem [2+1]/[3+2] Cycloaddition Sequence. Angew Chem 2011, 123, 3614. <>
  • Achard Thierry, Lepronier Aymeric, Gimbert Yves, Clavier Hervé, Giordano Laurent, Tenaglia Alphonse, Buono Gérard: A Regio- and Diastereoselective Platinum-Catalyzed Tandem [2+1]/[3+2] Cycloaddition Sequence. Angew Chem Int Ed 2011, 50, 3552. <>
  • Ackermann Lutz, Kapdi Anant R., Fenner Sabine, Kornhaaß Christoph, Schulzke Carola: Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates. Chem Eur J 2011, 17, 2965. <>
  • Christiansen Andrea, Selent Detlef, Spannenberg Anke, Köckerling Martin, Reinke Helmut, Baumann Wolfgang, Jiao Haijun, Franke Robert, Börner Armin: Heteroatom-Substituted Secondary Phosphine Oxides (HASPOs) as Decomposition Products and Preligands in Rhodium-Catalysed Hydroformylation. Chemistry A European Journal 2011, 17, 2120. <>
  • Martin David, Moraleda Delphine, Achard Thierry, Giordano Laurent, Buono Gérard: Assessment of the Electronic Properties of P ligands Stemming from Secondary Phosphine Oxides. Chemistry A European Journal 2011, 17, 12729. <>
  • Ackermann Lutz, Barfüsser Sebastian, Kornhaass Christoph, Kapdi Anant R.: C–H Bond Arylations and Benzylations on Oxazol(in)es with a Palladium Catalyst of a Secondary Phosphine Oxide. Org Lett 2011, 13, 3082. <>
  • Karanik Magdalena, Lesage Denis, Gimbert Yves, Nava Paola, Humbel Stéphane, Giordano Laurent, Buono Gérard, Tabet Jean-Claude: Do Platinum(II) and Palladium(II) Phosphinito Phosphinous Acids Generate the Same Type of Reactive Intermediate in Alkyne Coordination? A Gas-Phase Study with Phenylethyne and Propargyl Acetate. Organometallics 2011, 30, 4814. <>
  • Röhlich Christoph, Köhler Klaus: Macrocyclic Palladium(II) Complexes in CC Coupling Reactions: Efficient Catalysis by Controlled Temporary Release of Active Species. Synth Catal 2010, 352, 2263. <>
  • Christiansen Andrea, Li Chuanzhao, Garland Marc, Selent Detlef, Ludwig Ralf, Franke Robert, Börner Armin: Secondary Phosphane Oxides as Preligands in Rhodium-Catalyzed Hydroformylation. ChemCatChem 2010, 2, 1278. <>
  • Ackermann Lutz, Potukuchi Harish K., Kapdi Anant R., Schulzke Carola: Kumada-Corriu Cross-Couplings with 2-Pyridyl Grignard Reagents. Chem Eur J 2010, 16, 3300. <>
  • Xie Lan-Gui, Wang Zhong-Xia: Nickel-Catalyzed Cross-Coupling of Non-Activated or Functionalized Aryl Halides with Aryl Grignard Reagents. Chem Eur J 2010, 16, 10332. <>
  • Christiansen Andrea, Li Chuanzhao, Garland Marc, Selent Detlef, Ludwig Ralf, Spannenberg Anke, Baumann Wolfgang, Franke Robert, Börner Armin: On the Tautomerism of Secondary Phosphane Oxides. Eur J Org 2010, 2010, 2733. <>
  • Ackermann Lutz: Air-Stable Bifunctional HASPO Preligands for Metal-Catalyzed Cross-Couplings and Direct C-H Bond Arylations. Isr J Chem 2010, 50, 652. <>
  • Firouzabadi Habib, Iranpoor Nasser, Gholinejad Mohammad: 2-Aminophenyl diphenylphosphinite as an easily accessible ligand for heterogeneous palladium-catalyzed Suzuki–Miyaura reaction in water in the absence of any organic co-solvent. J Organomet Chem 2010, 695, 2093. <>
  • Das Pankaj, Bora Utpal, Tairai Archana, Sharma Chandan: Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki–Miyaura reaction. Tetrahetron Lett 2010, 51, 1479. <>
  • Ackermann Lutz: Metal-catalyzed direct alkylations of (hetero)arenes via C–H bond cleavages with unactivated alkyl halides. Chem Commun 2010, 46, 4866. <>
  • Ackermann Lutz, Potukuchi Harish Kumar: Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C–H bond functionalization nexus. Org Biomol Chem 2010, 8, 4503. <>
  • Ackermann Lutz: Transition-metal-catalyzed direct arylations via C–H bond cleavages. Pure and App Chemis 2010, 1. <>
  • Deng Guojun, Chen Wenwen, Li Chao-Jun: An Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes. Adv. Synth. Catal. 2009, 351, 353. <>
  • Ackermann Lutz, Vicente Rubén, Kapdi Anant R.: Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage. Angew Chem Int Ed 2009, 48, 9792. <>
  • Braun Leonie, Liptau Patrick, Kehr Gerald, Ugolotti Juri, Fr?hlich Roland, Erker Gerhard: Bis(diphenylphosphino)acetonitrile: Synthesis, ligand properties and application in catalytic carbon?carbon coupling. Dalton Trans 2007, 1409. <>
  • Ackermann Lutz, Born Robert, Spatz Julia H., Althammer Andreas, Gschrei Christian J.: Air-Stable Phosphine Oxides as Preligands for Catalytic Activation Reactions of C—Cl, C—F, and C—H Bonds. ChemInform 2006, 37. <>
  • Ackermann Lutz, Althammer Andreas: Air-Stable PinP(O)H as Preligand for Palladium-Catalyzed Kumada Couplings of Unactivated Tosylates. Org Lett 2006, 8, 3457. <>