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Halomethyl-cobalt(bis-acetylacetonate) for the controlled synthesis of functional polymers

Bibliographic reference Demarteau, Jérémy ; Kermagoret, Anthony ; German, Ian ; Cordella, Daniela ; Robeyns, Koen ; et. al. Halomethyl-cobalt(bis-acetylacetonate) for the controlled synthesis of functional polymers. In: Chemical Communications, Vol. 51, no. 76, p. 14334-14337 (2015)
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  1. Iqbal Javed, Bhatia Beena, Nayyar Naresh K., Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds, 10.1021/cr00026a008
  2. Schrauzer Gerhard N., Sibert J. W., Windgassen Richard J., Photochemical and thermal cobalt-carbon bond cleavage in alkylcobalamins and related organometallic compounds. Comparative study, 10.1021/ja01026a021
  3. Halpern Jack, Ng Flora T. T., Rempel Garry L., Metal-alkyl bond dissociation energies in organocobalt compounds related to vitamin B12 coenzymes, 10.1021/ja00517a083
  4. Tsou Tsung Ting, Loots Melanie, Halpern Jack, Kinetic determination of transition metal-alkyl bond dissociation energies: application to organocobalt compounds related to B12 coenzymes, 10.1021/ja00366a046
  5. Hay Benjamin P., Finke Richard G., Thermolysis of the cobalt-carbon bond of adenosylcobalamin. 2. Products, kinetics, and cobalt-carbon bond dissociation energy in aqueous solution, 10.1021/ja00276a020
  6. Pattenden Gerald, Simonsen Lecture. Cobalt-mediated radical reactions in organic synthesis, 10.1039/cs9881700361
  7. Gridnev Alexei A., Ittel Steven D., Catalytic Chain Transfer in Free-Radical Polymerizations, 10.1021/cr9901236
  8. Debuigne Antoine, Poli Rinaldo, Jérôme Christine, Jérôme Robert, Detrembleur Christophe, Overview of cobalt-mediated radical polymerization: Roots, state of the art and future prospects, 10.1016/j.progpolymsci.2008.11.003
  9. Peng Chi-How, Yang Tsung-Yao, Zhao Yaguang, Fu Xuefeng, Reversible deactivation radical polymerization mediated by cobalt complexes: recent progress and perspectives, 10.1039/c4ob01427h
  10. Schrauzer Gerhard N., Ribeiro Anthony, Lee Lian P., Ho Raymond K. Y., Novel Degradation Reactions of Halomethyl Derivatives of Bis(diacetyldioximato)cobalt, 10.1002/anie.197108072
  11. Randaccio Lucio, Bresciani-Pahor Nevenka, Toscano Paul J., Marzilli Luigi G., Angular distortions at the carbon bound to cobalt in coenzyme B12 models. Implications with regard to cobalt-carbon bond cleavage in coenzyme B12 and other alkylcobalamins, 10.1021/ja00411a014
  12. Randaccio Lucio., Bresciani-Pahor Nevenka., Toscano Paul J., Marzilli Luigi G., Bonding mode and trans influence of the nitromethyl ligand. Structure of trans-bis(dimethylglyoximato)(nitromethyl)(pyridine)cobalt(III), 10.1021/ic50222a068
  13. Bresciani-Pahor Nevenka, Randaccio Lucio, Summers M., Toscano P.J., Structural distortions in alkylcobaloximes containing triphenylphosphine as axial ligand. The X-ray structures of trans-bis(dimethylglyoximoto)(bromomethyl)(triphenylphosphine)cobalt(III) and trans-bis(dimethylglyoximato)(cyanomethyl)(triphenylphosphine)cobalt(III), 10.1016/s0020-1693(00)88940-9
  14. López Concepción, Alvarez Santiago, Font-Bardía Mercè, Solans Xavier, New organometallic cobaloximes containing an equatorial diphenylglyoximato(−1) ligand. Comparison between their properties and those of other B12 model compounds. Crystal structure of trans-[Co(dpgH)2(CH3)(pyridine)], 10.1016/0022-328x(91)86105-y
  15. Dolphin, Chem. Commun., 494 (1965)
  16. Clarke, Chem. Commun., 208 (1966)
  17. Clarke D. A., Dolphin D., Grigg R., Johnson A. W., Pinnock H. A., Alkyl-, aryl-, and acyl-metal(III) complexes of aetioporphyrin I, 10.1039/j39680000881
  18. Schrauzer Gerhard N., Organocobalt chemistry of vitamin B12 model compounds (cobaloximes), 10.1021/ar50004a001
  19. Ogoshi Hisanobu, Watanabe Ei-ichi, Koketsu Norihisa, Yoshida Zen-ichi, Synthesis and Properties of Organocobalt(III)octaethylporphyrins, 10.1246/bcsj.49.2529
  20. Schrauzer G. N., Windgassen R. J., Cobalamin Model Compounds. Preparation and Reactions of Substituted Alkyl- and Alkenylcobaloximes and Biochemical Implications, 10.1021/ja00985a006
  21. Brown Kenneth L., Brooks Harold B., Effects of axial ligation on the thermolysis of benzyl- and neopentylcobamides: analysis of the base-on effect, 10.1021/ic00018a011
  22. SMITH E. LESTER, MERVYN L., JOHNSON A. W., SHAW N., Partial Synthesis of Vitamin B12 Coenzyme and Analogues, 10.1038/1941175a0
  23. Schrauzer Gerhard N., Deutsch Erwin, Reactions of cobalt(I) supernucleophiles. The alkylation of vitamin B12s, cobaloximes(I), and related compounds, 10.1021/ja01040a041
  24. Schrauzer Gerhard N., Holland Robert J., Hydridocobaloximes, 10.1021/ja00735a040
  25. Schrauzer G. N., Holland R. J., Hydridocobalamin and a new synthesis of organocobalt derivatives of vitamin B12, 10.1021/ja00745a048
  26. Gridnev Alexei A., Ittel Steven D., Fryd Michael, Wayland Bradford B., Formation of organocobalt porphyrin complexes by reactions of cobalt(II) porphyrins with azoisobutyronitrile and organic substrates, 10.1039/c39930001010
  27. Gridnev Alexei A., Ittel Steven D., Fryd Michael, Wayland Bradford B., Formation of organocobalt porphyrin complexes from reactions of cobalt(II) porphyrins and dialkylcyanomethyl radicals with organic substrates: chemical trapping of a transient cobalt porphyrin hydride, 10.1021/om00036a029
  28. McCauley Kevin M., Wilson Scott R., van der Donk Wilfred A., Synthesis and Characterization of Chlorinated Alkenylcobaloximes To Probe the Mechanism of Vitamin B12-Catalyzed Dechlorination of Priority Pollutants, 10.1021/ic011023x
  29. Sherwood Roger K., Kent Catherine L., Patrick Brian O., McNeil W. Stephen, Controlled radical polymerisation of methyl acrylate initiated by a well-defined cobalt alkyl complex, 10.1039/b922030e
  30. Zhao Yaguang, Yu Mengmeng, Zhang Shuailin, Liu Yuchu, Fu Xuefeng, Visible Light Induced Living/Controlled Radical Polymerization of Acrylates Catalyzed by Cobalt Porphyrins, 10.1021/ma5014385
  31. Zhao Yaguang, Yu Mengmeng, Zhang Shuailin, Wu Zhenqiang, Liu Yuchu, Peng Chi-How, Fu Xuefeng, A well-defined, versatile photoinitiator (salen)Co–CO2CH3 for visible light-initiated living/controlled radical polymerization, 10.1039/c5sc00477b
  32. Li Shan, Bruin Bas de, Peng Chi-How, Fryd Michael, Wayland Bradford B., Exchange of Organic Radicals with Organo-Cobalt Complexes Formed in the Living Radical Polymerization of Vinyl Acetate, 10.1021/ja804010h
  33. Wayland Bradford B., Poszmik George, Mukerjee Shakti L., Fryd Michael, Living Radical Polymerization of Acrylates by Organocobalt Porphyrin Complexes, 10.1021/ja00096a080
  34. Arvanitopoulos, Polym. Prepr., 35, 549 (1994)
  35. Zhao Yaguang, Yu Mengmeng, Fu Xuefeng, Photo-cleavage of the cobalt–carbon bond: visible light-induced living radical polymerization mediated by organo-cobalt porphyrins, 10.1039/c3cc41466c
  36. Smith Weston J., Oien Nathan P., Hughes Robert M., Marvin Christina M., Rodgers Zachary L., Lee Junghyun, Lawrence David S., Cell-Mediated Assembly of Phototherapeutics, 10.1002/anie.201406216
  37. Shell Thomas A., Shell Jennifer R., Rodgers Zachary L., Lawrence David S., Tunable Visible and Near-IR Photoactivation of Light-Responsive Compounds by Using Fluorophores as Light-Capturing Antennas, 10.1002/anie.201308816
  38. Debuigne Antoine, Champouret Yohan, Jérôme Robert, Poli Rinaldo, Detrembleur Christophe, Mechanistic Insights into the Cobalt-Mediated Radical Polymerization (CMRP) of Vinyl Acetate with Cobalt(III) Adducts as Initiators, 10.1002/chem.200701867
  39. Hurtgen Marie, Detrembleur Christophe, Jerome Christine, Debuigne Antoine, Insight into Organometallic-Mediated Radical Polymerization, 10.1080/15583724.2011.566401
  40. Poli Rinaldo, Relationship between One-Electron Transition-Metal Reactivity and Radical Polymerization Processes, 10.1002/anie.200503785
  41. Poli Rinaldo, Allan Laura E.N., Shaver Michael P., Iron-mediated reversible deactivation controlled radical polymerization, 10.1016/j.progpolymsci.2014.06.003
  42. Poli Rinaldo, New Phenomena in Organometallic-Mediated Radical Polymerization (OMRP) and Perspectives for Control of Less Active Monomers, 10.1002/chem.201500015
  43. Debuigne Antoine, Morin Aurélie N., Kermagoret Anthony, Piette Yasmine, Detrembleur Christophe, Jérôme Christine, Poli Rinaldo, Key Role of Intramolecular Metal Chelation and Hydrogen Bonding in the Cobalt-Mediated Radical Polymerization ofN-Vinyl Amides, 10.1002/chem.201201456
  44. Piette Yasmine, Debuigne Antoine, Jérôme Christine, Bodart Vincent, Poli Rinaldo, Detrembleur Christophe, Cobalt-mediated radical (co)polymerization of vinyl chloride and vinyl acetate, 10.1039/c2py20413d
  45. Kermagoret Anthony, Debuigne Antoine, Jérôme Christine, Detrembleur Christophe, Precision design of ethylene- and polar-monomer-based copolymers by organometallic-mediated radical polymerization, 10.1038/nchem.1850
  46. Baisch Ulrich, Poli Rinaldo, Copper(I/II) and cobalt(II) coordination chemistry of relevance to controlled radical polymerization processes, 10.1016/j.poly.2008.03.022
  47. Poli Rinaldo, Radical Coordination Chemistry and Its Relevance to Metal-Mediated Radical Polymerization, 10.1002/ejic.201001364
  48. Maria Sébastien, Kaneyoshi Hiromu, Matyjaszewski Krzysztof, Poli Rinaldo, Effect of Electron Donors on the Radical Polymerization of Vinyl Acetate Mediated by [Co(acac)2]: Degenerative Transfer versus Reversible Homolytic Cleavage of an Organocobalt(III) Complex, 10.1002/chem.200601457
  49. Debuigne Antoine, Michaux Catherine, Jérôme Christine, Jérôme Robert, Poli Rinaldo, Detrembleur Christophe, Cobalt-Mediated Radical Polymerization of Acrylonitrile: Kinetics Investigations and DFT Calculations, 10.1002/chem.200800371
  50. Detrembleur Christophe, Versace Davy-Louis, Piette Yasmine, Hurtgen Marie, Jérôme Christine, Lalevée Jacques, Debuigne Antoine, Synthetic and mechanistic inputs of photochemistry into the bis-acetylacetonatocobalt-mediated radical polymerization of n-butyl acrylate and vinyl acetate, 10.1039/c1py00443c
  51. Chatgilialoglu C., Griller D., Lesage M., Tris(trimethylsilyl)silane. A new reducing agent, 10.1021/jo00250a051
  52. Ballestri M., Chatgilialoglu C., Clark K. B., Griller D., Giese B., Kopping B., Tris(trimethylsilyl)silane as a radical-based reducing agent in synthesis, 10.1021/jo00002a035
  53. Chatgilialoglu Chryssostomos, Lalevée Jacques, Recent Applications of the (TMS)3SiH Radical-Based Reagent, 10.3390/molecules17010527
  54. Evans D. F., 400. The determination of the paramagnetic susceptibility of substances in solution by nuclear magnetic resonance, 10.1039/jr9590002003
  55. Sur, J. Magn. Reson., 82, 169 (1989)
  56. Debuigne Antoine, Caille Jean-Raphaël, Jérôme Robert, Synthesis of End-Functional Poly(vinyl acetate) by Cobalt-Mediated Radical Polymerization, 10.1021/ma047726q
  57. Debuigne Antoine, Jérôme Christine, Detrembleur Christophe, Isoprene-Assisted Radical Coupling of (Co)polymers Prepared by Cobalt-Mediated Radical Polymerization, 10.1002/anie.200804880
  58. Debuigne Antoine, Poli Rinaldo, De Winter Julien, Laurent Pascal, Gerbaux Pascal, Dubois Philippe, Wathelet Jean-Paul, Jérôme Christine, Detrembleur Christophe, Cobalt-Mediated Radical Coupling (CMRC): An Unusual Route to Midchain-Functionalized Symmetrical Macromolecules, 10.1002/chem.200902618
  59. Debuigne Antoine, Hurtgen Marie, Detrembleur Christophe, Jérôme Christine, Barner-Kowollik Christopher, Junkers Thomas, Interpolymer radical coupling: A toolbox complementary to controlled radical polymerization, 10.1016/j.progpolymsci.2012.01.003
  60. Rostovtsev Vsevolod V., Green Luke G., Fokin Valery V., Sharpless K. Barry, A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes, 10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>;2-4
  61. Iha Rhiannon K., Wooley Karen L., Nyström Andreas M., Burke Daniel J., Kade Matthew J., Hawker Craig J., Applications of Orthogonal “Click” Chemistries in the Synthesis of Functional Soft Materials, 10.1021/cr900138t