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Pure Appl. Chem., 1992, Vol. 64, No. 3, pp. 335-342

http://dx.doi.org/10.1351/pac199264030335

Selected applications to organic synthesis of intramolecular C-H activation reactions by transition metals

M. Pfeffer

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  • Karami Kazem, Hosseini-Kharat Mahboubeh, Sadeghi-Aliabadi Hojjat, Lipkowski Janusz, Mirian Mina: In vitro cytotoxicity studies of palladacyclic complexes containing the symmetric diphosphine bridging ligand. Studies of their interactions with DNA and BSA. European Journal of Medicinal Chemistry 2014, 73, 8. <http://dx.doi.org/10.1016/j.ejmech.2013.11.042>
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  • Karami Kazem, Hosseini-Kharat Mahboubeh, Rizzoli Corrado, Tavakol Hossein, Lipkowski Janusz: Structural and theoretical studies of mono and di-insertion of symmetric alkynes into the Pd–C σ bond of cyclopalladated secondary (tert-butyl and ethyl) benzylamines. Journal of Organometallic Chemistry 2014, 752, 152. <http://dx.doi.org/10.1016/j.jorganchem.2013.11.030>
  • Oliva-Madrid María-José, Garcı́a-López José-Antonio, Saura-Llamas Isabel, Bautista Delia, Vicente José: Reactivity of Eight-Membered Palladacycles Arising from Monoinsertion of Alkynes into the Pd–C bond of Ortho-Palladated Phenethylamines toward Unsaturated Molecules. Synthesis of Dihydro-3-Benzazocinones, N7-amino Acids, N7-amino Esters, and 3-Benzazepines. Organometallics 2014, 33, 19. <http://dx.doi.org/10.1021/om4010059>
  • Chen Shuli, Chiew Jun Xuan, Pullarkat Sumod A., Li Yongxin, Leung Pak-Hing: Stability and Reactivity of Cyclometallated Naphthylamine Complexes in Pd-C Bond Insertion Reactions with Coordinated Alkynylphosphanes. Eur. J. Inorg. Chem. 2013, 2013, 5487. <http://dx.doi.org/10.1002/ejic.201300834>
  • Sabounchei Seyyed Javad, Ahmadi Mohsen: Palladacycle phosphine complexes as homogeneous catalysts for the Heck cross-coupling reaction at low catalyst loading under aerobic conditions. Inorganica Chimica Acta 2013, 405, 15. <http://dx.doi.org/10.1016/j.ica.2013.04.048>
  • Sabater Sara, Mata Jose A., Peris Eduardo: Chiral Palladacycles with N-Heterocyclic Carbene Ligands as Catalysts for Asymmetric Hydrophosphination. Organometallics 2013, 32, 1112. <http://dx.doi.org/10.1021/om400007a>
  • Frutos-Pedreño Roberto, González-Herrero Pablo, Vicente José, Jones Peter G.: Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides. Insertion of CO, XyNC, and Alkynes into the Pd–C Bond. Synthesis of Seven- and Nine-Membered Palladacycles and Benzazepine- and Benzazonine-Based Heterocycles. Organometallics 2013, 32, 1892. <http://dx.doi.org/10.1021/om4000192>
  • Saxena Priya, Thirupathi Natesan, Nethaji Munirathinam: Insertion Reactions of Six-Membered Cyclopalladated N,N′,N″-Triarylguanidine, [Pd{κ2(C,N)-C6H3Me-3(NHC(NHAr)(═NAr))-2}(μ-Br)]2 (Ar = 2-MeC6H4) with PhC≡C—C(O)OR (R = Me and Et): A Gateway to Second Orthopalladation through Novel Rearrangements. Organometallics 2013, 32, 7580. <http://dx.doi.org/10.1021/om4010719>
  • Kapdi Anant R., Karbelkar Amruta, Naik Minal, Pednekar Suhas, Fischer Christian, Schulzke Carola, Tromp Moniek: Efficient synthesis of coumarin-based tetra and pentacyclic rings using phospha-palladacycles. RSC Adv. 2013, 3, 20905. <http://dx.doi.org/10.1039/c3ra43821j>
  • Colquhoun Victoria P., Schildbach Daniel, Martín-Romo Raquel, Strohmann Carsten, Villafañe Fernando: Syntheses, Dynamic Behaviour and Theoretical Studies of [(Piperidinomethyl)silyl]methyl-Cyclopalladated Dimetallic Complexes. Eur. J. Inorg. Chem. 2012, 2012, 3427. <http://dx.doi.org/10.1002/ejic.201200257>
  • Pal Samudranil, Rao A.R. Balavardhana: Cyclopalladated complexes with 9-anthraldehyde aroylhydrazones: Synthesis, properties and structures. J Organomet Chem 2012, 701, 62. <http://dx.doi.org/10.1016/j.jorganchem.2011.12.018>
  • Frutos-Pedreño Roberto, González-Herrero Pablo, Vicente José, Jones Peter G.: Sequential Insertion of Alkynes and CO or Isocyanides into the Pd–C Bond of Cyclopalladated Phenylacetamides. Synthesis of Eight-Membered Palladacycles, Benzo[d]azocine-2,4(1H,3H)-diones, and Highly Functionalized Acrylonitrile and Acrylamide Derivatives. Organomettalics 2012, 31, 3361. <http://dx.doi.org/10.1021/om300151n>
  • Boutadla Youcef, Davies David L., Jones Rachel C., Singh Kuldip: The Scope of Ambiphilic Acetate-Assisted Cyclometallation with Half-Sandwich Complexes of Iridium, Rhodium and Ruthenium. Chem Eur J 2011, 17, 3438. <http://dx.doi.org/10.1002/chem.201002604>
  • Chen Shuli, Pullarkat Sumod A., Li Yongxin, Leung Pak-Hing: Synthesis of Homo- and Hetero-Bimetallic Arsenic Complexes by Means of Regioselective Monoinsertion of Alkynylarsane into the Pd-C Bond of a Palladacycle. Eur J Inorg Chem 2011, 2011, 3111. <http://dx.doi.org/10.1002/ejic.201100208>
  • Butschke Burkhard, Schwarz Helmut: On the Activation of Chloromethanes by Cyclometalated [Pt(bipy – H)]+ in the Gas Phase: A Mechanistic Study. International Journal of Mass Spectrometry 2011, 306, 108. <http://dx.doi.org/10.1016/j.ijms.2010.08.030>
  • Hajipour Abdol R., Rafiee Fatemeh: Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction. J Organomet Chem 2011, 696, 2669. <http://dx.doi.org/10.1016/j.jorganchem.2011.03.023>
  • Ghavale Ninad, Dey Sandip, Wadawale Amey, Jain Vimal K.: Syntheses of platinum(II) complexes of cyclo-octenyl group and isolation of a self-assembled oxo-bridged macrocyclic complex [Pt4(Spy)4(C8H12-O-C8H12)2]. j organometall chem 2011. <http://dx.doi.org/10.1016/j.jorganchem.2011.07.025>
  • Hajipour Abdol Reza, Rafiee Fatemeh, Rouho Arnold E.: Applications of a monomeric orthopalladate complex containing mixed phosphorus–nitrogen donors in the Heck reaction. Tet Letts 2011, 52, 4782. <http://dx.doi.org/10.1016/j.tetlet.2011.07.036>
  • Cuesta Luciano, Prat Dune, Soler Tatiana, Navarro Rafael, Urriolabeitia Esteban P.: Novel Cyclopalladated Imino-thiophenes: Synthesis and Reactivity Toward Alkynes and Carbon Monoxide. Inorg. Chem. 2011, 50, 8598. <http://dx.doi.org/10.1021/ic201158v>
  • Crimmin Mark R., Colby Denise A., Ellman Jonathan A., Bergman Robert G.: Synthesis and coordination chemistry of tri-substituted benzamidrazones. Dalton Trans 2011, 40, 514. <http://dx.doi.org/10.1039/c0dt01267j>
  • Echavarren Antonio M., Cárdenas Diego J., Castaño Ana M., Cuerva Juan M., Mateo Cristina: Design and Synthetic Applications of New Heterometallacycles. Bull Soc Chim Belges 2010, 103, 549. <http://dx.doi.org/10.1002/bscb.19941030906>
  • Vicente José, Abad José-Antonio, López-Sáez María-José, Jones Peter G., Bautista Delia: Reactivity of ortho-Substituted Aryl–Palladium Complexes towards Carbodiimides, Isothiocyanates, Nitriles, and Cyanamides. Chem Eur J 2010, 16, 661. <http://dx.doi.org/10.1002/chem.200901828>
  • Butschke Burkhard, Ghassemi Tabrizi Shadan, Schwarz Helmut: Ion-Molecule Reactions of “Rollover” Cyclometalated [Pt(bipy−H)]+ (bipy=2,2′-bipyridine) with Dimethyl Ether in Comparison with Dimethyl Sulfide: An Experimental/Computational Study. Chemistry A European Journal 2010, 16, 3962. <http://dx.doi.org/10.1002/chem.200902742>
  • PFEFFER M.: ChemInform Abstract: Selected Applications to Organic Synthesis of Intramolecular C-H Activation Reactions by Transition Metals. ChemInform 2010, 23, no. <http://dx.doi.org/10.1002/chin.199232278>
  • Ghavale Ninad, Wadawale Amey, Dey Sandip, Jain Vimal K.: Synthesis, structures and spectroscopic properties of platinum complexes containing orthometalated 2-phenylpyridine. J Organomet Chem 2010, 695, 1237. <http://dx.doi.org/10.1016/j.jorganchem.2010.01.035>
  • Djukic Jean-Pierre, Sortais Jean-Baptiste, Barloy Laurent, Pfeffer Michel: Cycloruthenated Compounds - Synthesis and Applications. Eur J Inorg Chem 2009, 2009, 817. <http://dx.doi.org/10.1002/ejic.200801016>
  • Hajipour Abdol R., Karami Kazem, Pirisedigh Azadeh, Ruoho Arnold E.: Synthesis and characterization of new Pd(II) complexes of l-ethylphenylalanate. Amino Acids 2009, 37, 537. <http://dx.doi.org/10.1007/s00726-009-0258-3>
  • Hajipour Abdol R., Karami Kazem, Pirisedigh Azadeh, Ruoho Arnold E.: Application of dimeric orthopalladate complex of homoveratrylamine as an efficient catalyst in the Heck cross-coupling reaction. J Organomet Chem 2009, 694, 2548. <http://dx.doi.org/10.1016/j.jorganchem.2009.04.003>
  • Albert Joan, D’Andrea Lucía, García Graciela, Granell Jaume, Rahmouni Abdelouahab, Font-Bardia Mercè, Calvet Teresa: Cyclopalladation of (E)-N-(2,6-dichlorobenzylidene)(naphthalen-1-yl)methanamine: Synthesis and X-ray molecular structure of [κ2-N,C1-η2-C3,C4-Pd{(PhCCPh)2–C10H6–CH2–NCH–(2,6-Cl2C6H3)}Cl]·CH2Cl2. J Polyhedron 2009, 28, 2559. <http://dx.doi.org/10.1016/j.poly.2009.05.021>
  • Ramírez Paola, Contreras Raúl, Valderrama Mauricio, Carmona Daniel, Lahoz Fernando J., Balana Ana I.: Cyclometallated platinum(II) complexes containing the chiral ligand [2-(diphenyl-phosphanyl)-benzylidene]-(1-phenyl-ethyl)-amine: Synthesis and molecular structures of the compounds [PtCl(Me){κ2-(R)-Ph2P(C6H4)CHNCH(Ph)Me-P,N}] and [Pt{κ3-(S)-Ph2P(C6H4)CHNCH(C6H4)Me-P,N,C}Py]BF4. J Organomet Chem 2008, 693, 349. <http://dx.doi.org/10.1016/j.jorganchem.2007.10.032>
  • Joshaghani Mohammad, Daryanavard Marzieh, Rafiee Ezzat, Nadri Shirin: Synthesis and applications of a new palladacycle as a high active catalyst in the Suzuki couplings. J Organomet Chem 2008, 693, 3135. <http://dx.doi.org/10.1016/j.jorganchem.2008.07.003>
  • Aragay Gemma, Pons Josefina, García-Antón Jordi, Solans Xavier, Font-Bardia Mercè, Ros Josep: Synthesis, characterization and X-ray crystal structure determination of cyclopalladated [Csp2,N,N′]−, zwitterionic and chelated compounds in the reaction of 3,5-diphenyl-N-alkylaminopyrazole derived ligands with Pd(II). J Organomet Chem 2008, 693, 3396. <http://dx.doi.org/10.1016/j.jorganchem.2008.07.038>
  • Amatore Christian, Cammoun Chama, Jutand Anny: Electrochemical Recycling of Benzoquinone in the Pd/Benzoquinone-Catalyzed Heck-Type Reactions from Arenes. Adv Synth Catal 2007, 349, 292. <http://dx.doi.org/10.1002/adsc.200600389>
  • Bröring Martin, Kleeberg Christian, Cónsul Tejero Esther: Syntheses, Structures and Coordination Modes of Acetatopalladium(II) Complexes with 1,3-Bis(2-arylimino)isoindoline Ligands of Different Steric Influence. Eur J Inorg Chem 2007, 2007, 3208. <http://dx.doi.org/10.1002/ejic.200700286>
  • Omae Iwao: Three types of reactions with intramolecular five-membered ring compounds in organic synthesis. J Organomet Chem 2007, 692, 2608. <http://dx.doi.org/10.1016/j.jorganchem.2007.02.036>
  • Albert Joan, D’Andrea Lucía, Granell Jaume, Tavera Raquel, Font-Bardia Mercè, Solans Xavier: Synthesis and reactivity towards carbon monoxide of an optically active endo five-membered ortho-cyclopalladated imine: X-ray molecular structure of trans-(μ-Cl)2[Pd(κ2-C,N-(R)-C6H4-CHN-CHMe-Ph)]2. J Organomet Chem 2007, 692, 3070. <http://dx.doi.org/10.1016/j.jorganchem.2007.03.035>
  • Albert Joan, D’Andrea Lucía, Granell Jaume, Zafrilla Javier, Font-Bardia Mercè, Solans Xavier: Reactivity of cyclopalladated compounds derived from biphenyl-2-ylamine towards carbon monoxide, tbutyl isocyanide and alkynes. J Organomet Chem 2007, 692, 4895. <http://dx.doi.org/10.1016/j.jorganchem.2007.07.002>
  • Br?ring Martin, Kleeberg Christian: Cyclometalation vs. Werner-type coordination of sterically enforced palladium(ii)-1,3-bis(pyridyl-2-imino)isoindolines (Pd-BPIs). Dalton Trans 2007, 1101. <http://dx.doi.org/10.1039/b700400a>
  • Vicente José, Saura-Llamas Isabel: ORTHO-PALLADATION OF PRIMARY AMINES: THE MYTH DISPELLED. Comments Inorg Chem 2007, 28, 39. <http://dx.doi.org/10.1080/02603590701394766>
  • Zuccaccia Cristiano, Bellachioma Gianfranco, Cardaci Giuseppe, Macchioni Alceo, Binotti Barbara, Carfagna Carla: Synthesis, Interionic Structure, and Reactivity toward CO andp-Methylstyrene of Palladacyclic Compounds Bearingα-Diimine Ligands. HCA 2006, 89, 1524. <http://dx.doi.org/10.1002/hlca.200690155>
  • Omae Iwao: Intramolecular five-membered ring compounds and their applications. Coord Chem Rev - 2004, 248, 995. <http://dx.doi.org/10.1016/j.ccr.2004.05.011>
  • Tomazela Daniela M., Gozzo Fábio C., Ebeling Gunter, Livotto Paolo R., Eberlin Marcos N., Dupont Jairton: On the identification of ionic species of neutral halogen dimers, monomers and pincer type palladacycles in solution by electrospray mass and tandem mass spectrometry. Inorg Chim Ada 2004, 357, 2349. <http://dx.doi.org/10.1016/j.ica.2004.01.011>
  • Dupont Jairton, Pfeffer Michel, Spencer John: Palladacycles − An Old Organometallic Family Revisited: New, Simple, and Efficient Catalyst Precursors for Homogeneous Catalysis. Eur J Inorg Chem 2001, 2001, 1917. <http://dx.doi.org/10.1002/1099-0682(200108)2001:8<1917::AID-EJIC1917>3.0.CO;2-M>
  • Alami Mouad, Amatore Christian, Bensalem Samia, Choukchou-Brahim Abdelharim, Jutand Anny: Kinetics of the Oxidative Addition ofortho-Substituted Aryl Halides to Palladium(0) Complexes. Eur J Inorg Chem 2001, 2001, 2675. <http://dx.doi.org/10.1002/1099-0682(200109)2001:10<2675::AID-EJIC2675>3.0.CO;2-J>
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