Organocobalt complexes as sources of carbon-centered radicals for organic and polymer chemistries

[en] Organocobalt(III) complexes (R-CoIII), defined as cobalt complexes featuring a carbon−cobalt bond, are largely used to produce carbon-centered radicals by homolytic cleavage of their C−Co bond under mild conditions. They are key compounds in cutting-edge developments in the fields of organic chemistry, biochemistry, medical research, radical reactions, and organometallic chemistry. This is the first Review of the use of R-CoIII in both organic and polymer chemistries. Although pioneering works in organic synthesis have largely contributed to the implementation of R-CoIII in polymer design, the two fields have evolved independently, with many breakthroughs on both sides. The main motivation of this Review is to confront both fields to stimulate cross-fertilization. It notably describes the most important synthetic pathways for R-CoIII, the influence of the ligand structure and the environment of the complex on the C−Co bond strength, the modes of formation of the radicals, and the most relevant R-CoIII-promoted radical reactions, with a focus on the main reaction mechanisms.

Research Center/Unit :

CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
Center for Education and Research on Macromolecules (CERM), Belgium

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Demarteau, Jérémy; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Debuigne, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Language :

English

Title :

Organocobalt complexes as sources of carbon-centered radicals for organic and polymer chemistries

Publication date :

26 June 2019

Journal title :

Chemical Reviews

ISSN :

0009-2665

eISSN :

1520-6890

Publisher :

American Chemical Society, United States - District of Columbia

Volume :

119

Issue :

Pages :

6906-6955

Peer reviewed :

Peer Reviewed verified by ORBi

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique
FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture
BELSPO - Politique scientifique fédérale
EOS - The Excellence Of Science Program

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since 11 April 2019

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140

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Kermagoret, A.; Wenn, B.; Debuigne, A.; Jerome, C.; Junkers, T.; Detrembleur, C. Improved Photo-Induced Cobalt-Mediated Radical Polymerization in Continuous Flow Photoreactors. Polym. Chem. 2015, 6, 3847-3857, 10.1039/C5PY00299K
Demarteau, J.; Améduri, B.; Ladmiral, V.; Mees, M. A.; Hoogenboom, R.; Debuigne, A.; Detrembleur, C. Controlled Synthesis of Fluorinated Copolymers via Cobalt-Mediated Radical Copolymerization of Perfluorohexylethylene and Vinyl Acetate. Macromolecules 2017, 50, 3750-3760, 10.1021/acs.macromol.7b00578
Piette, Y.; Debuigne, A.; Jerôme, C.; Bodart, V.; Poli, R.; Detrembleur, C. Cobalt-Mediated Radical (Co)polymerization of Vinyl Chloride and Vinyl Acetate. Polym. Chem. 2012, 3, 2880-2891, 10.1039/c2py20413d
Banerjee, S.; Ladmiral, V.; Debuigne, A.; Detrembleur, C.; Poli, R.; Améduri, B. Organometallic-Mediated Radical Polymerization of Vinylidene Fluoride. Angew. Chem., Int. Ed. 2018, 57, 2934-2937, 10.1002/anie.201712347
Falireas, P. G.; Ladmiral, V.; Debuigne, A.; Detrembleur, C.; Poli, R.; Ameduri, B. Straightforward Synthesis of Well-Defined Poly(vinylidene Fluoride) and Its Block Copolymers by Cobalt-Mediated Radical Polymerization. Macromolecules 2019, 52, 1266-1276, 10.1021/acs.macromol.8b02252
Detrembleur, C.; Debuigne, A.; Hurtgen, M.; Jérôme, C.; Pinaud, J.; Fèvre, M.; Coupillaud, P.; Vignolle, J.; Taton, D. Synthesis of 1-Vinyl-3-Ethylimidazolium-Based Ionic Liquid (Co)polymers by Cobalt-Mediated Radical Polymerization. Macromolecules 2011, 44, 6397-6404, 10.1021/ma201041s
Cordella, D.; Kermagoret, A.; Debuigne, A.; Riva, R.; German, I.; Isik, M.; Jérôme, C.; Mecerreyes, D.; Taton, D.; Detrembleur, C. Direct Route to Well-Defined Poly(ionic Liquid)s by Controlled Radical Polymerization in Water. ACS Macro Lett. 2014, 3, 1276-1280, 10.1021/mz500721r
Cordella, D.; Kermagoret, A.; Debuigne, A.; Jerome, C.; Mecerreyes, D.; Isik, M.; Taton, D.; Detrembleur, C. All Poly(ionic Liquid)-Based Block Copolymers by Sequential Controlled Radical Copolymerization of Vinylimidazolium Monomers. Macromolecules 2015, 48, 5230-5243, 10.1021/acs.macromol.5b01013
Weiss-Maurin, M.; Cordella, D.; Jerome, C.; Taton, D.; Detrembleur, C. Direct One-Pot Synthesis of Poly(ionic Liquid) Nanogels by Cobalt-Mediated Radical Cross-Linking Copolymerization in Organic or Aqueous Media. Polym. Chem. 2016, 7, 2521-2530, 10.1039/C6PY00112B
Cordella, D.; Debuigne, A.; Jerome, C.; Kochovski, Z.; Taton, D.; Detrembleur, C. One-Pot Synthesis of Double Poly(Ionic Liquid) Block Copolymers by Cobalt-Mediated Radical Polymerization-Induced Self-Assembly (CMR-PISA) in Water. Macromol. Rapid Commun. 2016, 37, 1181-1187, 10.1002/marc.201600039
Patil, N.; Cordella, D.; Aqil, A.; Debuigne, A.; Admassie, S.; Jerome, C.; Detrembleur, C. Surface-and Redox-Active Multifunctional Polyphenol-Derived Poly(ionic Liquid)s: Controlled Synthesis and Characterization. Macromolecules 2016, 49, 7676-7691, 10.1021/acs.macromol.6b01857
Cordella, D.; Ouhib, F.; Aqil, A.; Defize, T.; Jerome, C.; Serghei, A.; Drockenmuller, E.; Aissou, K.; Taton, D.; Detrembleur, C. Fluorinated Poly(ionic Liquid) Diblock Copolymers Obtained by Cobalt-Mediated Radical Polymerization-Induced Self-Assembly. ACS Macro Lett. 2017, 6, 121-126, 10.1021/acsmacrolett.6b00899
Debuigne, A.; Willet, N.; Jerome, R.; Detrembleur, C. Amphiphilic Poly(vinyl Acetate)-B-poly(N-Vinylpyrrolidone) and Novel Double Hydrophilic Poly(vinyl Alcohol)-B-poly(N-Vinylpyrrolidone) Block Copolymers Prepared by Cobalt-Mediated Radical Polymerization. Macromolecules 2007, 40, 7111-7118, 10.1021/ma0712908
Debuigne, A.; Morin, A. N. A. N.; Kermagoret, A.; Piette, Y.; Detrembleur, C.; Jérôme, C.; Poli, R. Key Role of Intramolecular Metal Chelation and Hydrogen Bonding in the Cobalt-Mediated Radical Polymerization of N-Vinyl Amides. Chem.-Eur. J. 2012, 18, 12834-12844, 10.1002/chem.201201456
Kermagoret, A.; Fustin, C.-A.; Bourguignon, M.; Detrembleur, C.; Jerome, C.; Debuigne, A. One-Pot Controlled Synthesis of Double Thermoresponsive N-Vinylcaprolactam-Based Copolymers with Tunable LCSTs. Polym. Chem. 2013, 4, 2575-2583, 10.1039/c3py00134b
Drean, M.; Guegan, P.; Detrembleur, C.; Jerome, C.; Rieger, J.; Debuigne, A. Controlled Synthesis of Poly(vinylamine)-Based Copolymers by Organometallic-Mediated Radical Polymerization. Macromolecules 2016, 49, 4817-4827, 10.1021/acs.macromol.6b00992
Kermagoret, A.; Mathieu, K.; Thomassin, J.-M.; Fustin, C.-A.; Duchene, R.; Jerome, C.; Detrembleur, C.; Debuigne, A. Double Thermoresponsive Di-and Triblock Copolymers Based on N-Vinylcaprolactam and N-Vinylpyrrolidone: Synthesis and Comparative Study of Solution Behavior. Polym. Chem. 2014, 5, 6534-6544, 10.1039/C4PY00852A
Mumtaz, M.; Labrugère, C.; Cloutet, E.; Cramail, H. Synthesis of Poly(3,4-Ethylenedioxythiophene) Latexes Using poly(N-Vinylpyrrolidone)-Based Copolymers as Reactive Stabilizers. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3841-3855, 10.1002/pola.24171
Bryaskova, R.; Willet, N.; Debuigne, A.; Jérôme, R.; Detrembleur, C. Synthesis of Poly(vinyl Acetate)-B-Polystyrene and Poly(vinyl Alcohol)-B-Polystyrene Copolymers by Cobalt-Mediated Radical Polymerization. J. Polym. Sci., Part A: Polym. Chem. 2006, 45, 81-89, 10.1002/pola.21806
Hurtgen, M.; Debuigne, A.; Jérôme, C.; Detrembleur, C. Solving the Problem of Bis(acetylacetonato)cobalt(II)-Mediated Radical Polymerization (CMRP) of Acrylic Esters. Macromolecules 2010, 43, 886-894, 10.1021/ma902310c
Debuigne, A.; Warnant, J.; Jérôme, R.; Voets, I.; De Keizer, A.; Stuart, M. A. C.; Detrembleur, C. Synthesis of Novel Well-Defined Poly (Vinyl Acetate)-B-Poly (Acrylonitrile) and Derivatized Water-Soluble Poly (Vinyl Alcohol)-B-Poly (Acrylic Acid) Block Copolymers by Cobalt-Mediated Radical Polymerization. Macromolecules 2008, 41, 2353-2360, 10.1021/ma702341v
Debuigne, A.; Jérôme, C.; Detrembleur, C. Isoprene-Assisted Radical Coupling of (Co)polymers Prepared by Cobalt-Mediated Radical Polymerization. Angew. Chem., Int. Ed. 2009, 48, 1422-1424, 10.1002/anie.200804880
Bryaskova, R.; Willet, N.; Duwez, A. S.; Debuigne, A.; Lepot, L.; Gilbert, B.; Jerome, C.; Jerome, R.; Detrembleur, C. Gold-Loaded Carbon Nanoparticles from Poly(vinyl Alcohol)-B-Poly(acrylonitrile) Non-Shell-Cross-Linked Micelles. Chem.-Asian J. 2009, 4, 1338-1345, 10.1002/asia.200900130
Banerjee, S.; Ladmiral, V.; Ameduri, B.; Debuigne, A.; Detrembleur, C.; Rahaman, S. M. W.; Poli, R. Organometallic-Mediated Alternating Radical Copolymerization of Tert-Butyl-2-Trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof. Macromol. Rapid Commun. 2017, 38, 1700203, 10.1002/marc.201700203
Detrembleur, C.; Stoilova, O.; Bryaskova, R.; Debuigne, A.; Mouithys-Mickalad, A.; Jérôme, R. Preparation of Well-Defined PVOH/C60 Nanohybrids by Cobalt-Mediated Radical Polymerization of Vinyl Acetate. Macromol. Rapid Commun. 2006, 27, 498-504, 10.1002/marc.200500871
Thomassin, J. M.; Molenberg, I.; Huynen, I.; Debuigne, A.; Alexandre, M.; Jerome, C.; Detrembleur, C. Locating Carbon Nanotubes (CNTs) at the Surface of Polymer Microspheres Using Poly(vinyl Alcohol) Grafted CNTs as Dispersion Co-Stabilizers. Chem. Commun. 2010, 46, 3330-3332, 10.1039/c000125b
Detrembleur, C.; Debuigne, A.; Altintas, O.; Conradi, M.; Wong, E. H. H.; Jérôme, C.; Barner-Kowollik, C.; Junkers, T. Synthesis of Star and H-Shape Polymers via a Combination of Cobalt-Mediated Radical Polymerization and Nitrone-Mediated Radical Coupling Reactions. Polym. Chem. 2012, 3, 135-147, 10.1039/C1PY00297J
Detrembleur, C.; Debuigne, A.; Bryaskova, R.; Charleux, B.; Jérôme, R. Cobalt-Mediated Radical Polymerization of Vinyl Acetate in Miniemulsion: Very Fast Formation of Stable Poly(vinyl Acetate) Latexes at Low Temperature. Macromol. Rapid Commun. 2006, 27, 37-41, 10.1002/marc.200500645
Bryaskova, R.; Detrembleur, C.; Debuigne, A.; Jerome, R. Cobalt-Mediated Radical Polymerization (CMRP) of Vinyl Acetate Initiated by Redox Systems: Toward the Scale-Up of CMRP. Macromolecules 2006, 39, 8263-8268, 10.1021/ma060339r
Debuigne, A.; Schoumacher, M.; Willet, N.; Riva, R.; Zhu, X.; Rutten, S.; Jerome, C.; Detrembleur, C. New Functional poly(N-Vinylpyrrolidone) Based (Co)polymers via Photoinitiated Cobalt-Mediated Radical Polymerization. Chem. Commun. 2011, 47, 12703-12705, 10.1039/c1cc15471k
Ding, D.; Pan, X.; Zhang, Z.; Li, N.; Zhu, J.; Zhu, X. A Degradable Copolymer of 2-Methylene-1,3-Dioxepane and Vinyl Acetate by Photo-Induced Cobalt-Mediated Radical Polymerization. Polym. Chem. 2016, 7, 5258-5264, 10.1039/C6PY01061J
Kumar, K. S. S.; Gnanou, Y.; Champouret, Y.; Daran, J. C.; Poli, R. Radical Polymerization of Vinyl Acetate with bis(tetramethylheptadionato)cobalt(II): Coexistence of Three Different Mechanisms. Chem.-Eur. J. 2009, 15, 4874-4885, 10.1002/chem.200802388
Bellan, E. V.; Thevenin, L.; Gayet, F.; Fliedel, C.; Poli, R. Catalyzed Chain Transfer in Vinyl Acetate Polymerization Mediated by 9-Oxyphenalenone Cobalt(II) Complexes. ACS Macro Lett. 2017, 6, 959-962, 10.1021/acsmacrolett.7b00551
Banerjee, S.; Bellan, V. E.; Gayet, F.; Debuigne, A.; Detrembleur, C.; Poli, R.; Améduri, B.; Ladmiral, V. Bis(formylphenolato)cobalt(II)-Mediated Alternating Radical Copolymerization of Tert-Butyl 2-Trifluoromethylacrylate with Vinyl Acetate. Polymers 2017, 9, 702, 10.3390/polym9120702
Langlotz, B. K.; Lloret Fillol, J.; Gross, J. H.; Wadepohl, H.; Gade, L. H. Living Radical Polymerization of Acrylates Mediated by 1,3-bis(2-pyridylimino)isoindolatocobalt(II) Complexes: Monitoring the Chain Growth at the Metal. Chem.-Eur. J. 2008, 14, 10267-10279, 10.1002/chem.200801373
Hurtgen, M.; Debuigne, A.; Fustin, C. A.; Jérôme, C.; Detrembleur, C. Organometallic-Mediated Radical Polymerization: Unusual Route toward (Quasi-) Diblock Graft Copolymers Starting from a Mixture of Monomers of Opposed Reactivity. Macromolecules 2011, 44, 4623-4631, 10.1021/ma200845m
Stiernet, P.; Dréan, M.; Jérôme, C.; Midoux, P.; Guégan, P.; Rieger, J.; Debuigne, A. Tailor-Made Poly(vinylamine)s via Thermal or Photochemical Organometallic Mediated Radical Polymerization. ACS Symp. Ser. 2018, 1284, 349-363, 10.1021/bk-2018-1284.ch017
Stiernet, P.; Jerome, C.; Debuigne, A. Precision Design of Vinyl Amine and Vinyl Alcohol-Based Copolymers via Cobalt-Mediated Radical Polymerization. Polym. Chem. 2019, 10.1039/C9PY00020H
Scholten, P. B. V.; Demarteau, J.; Gennen, S.; De Winter, J.; Grignard, B.; Debuigne, A.; Meier, M. A. R.; Detrembleur, C. Merging CO2-Based Building Blocks with Cobalt-Mediated Radical Polymerization for the Synthesis of Functional Poly(vinyl Alcohol)s. Macromolecules 2018, 51, 3379-3393, 10.1021/acs.macromol.8b00492
Scholten, P. B. V; Detrembleur, C.; Meier, M. A. R. Plant-Based Nonactivated Olefins: A New Class of Renewable Monomers for Controlled Radical Polymerization. ACS Sustainable Chem. Eng. 2019, 7, 2751-2762, 10.1021/acssuschemeng.8b05926
Kermagoret, A.; Chau, N. D. Q.; Grignard, B.; Cordella, D.; Debuigne, A.; Jerome, C.; Detrembleur, C. Cobalt-Mediated Radical Polymerization of Vinyl Acetate and Acrylonitrile in Supercritical Carbon Dioxide. Macromol. Rapid Commun. 2016, 37, 539-544, 10.1002/marc.201500629
Debuigne, A.; Poli, R.; De Winter, J.; Laurent, P.; Gerbaux, P.; Wathelet, J.-P.; Jérôme, C.; Detrembleur, C. Effective Cobalt-Mediated Radical Coupling (CMRC) of Poly(vinyl Acetate) and Poly(N-Vinylpyrrolidone) (Co)polymer Precursors. Macromolecules 2010, 43, 2801-2813, 10.1021/ma902610m
Debuigne, A.; Poli, R.; De Winter, J.; Laurent, P.; Gerbaux, P.; Dubois, P.; Wathelet, J.-P.; Jérôme, C.; Detrembleur, C. Cobalt-Mediated Radical Coupling (CMRC): An Unusual Route to Midchain-Functionalized Symmetrical Macromolecules. Chem.-Eur. J. 2010, 16, 1799-1811, 10.1002/chem.200902618
Debuigne, A.; Hurtgen, M.; Jerome, C.; Detrembleur, C. Radical Coupling of Polymers Formed by Cobalt-Mediated Radical Polymerization. ACS Symp. Ser. 2012, 1100, 217-230, 10.1021/bk-2012-1100.ch014
Debuigne, A.; Hurtgen, M.; Detrembleur, C.; Jerome, C.; Barner-Kowollik, C.; Junkers, T. Interpolymer Radical Coupling: A Toolbox Complementary to Controlled Radical Polymerization. Prog. Polym. Sci. 2012, 37, 1004-1030, 10.1016/j.progpolymsci.2012.01.003
Debuigne, A.; Detrembleur, C.; Jérome, C.; Junkers, T. Straightforward Synthesis of Symmetrical Multiblock Copolymers by Simultaneous Block Extension and Radical Coupling Reactions. Macromolecules 2013, 46, 8922-8931, 10.1021/ma401918t
Demarteau, J.; De Winter, J.; Detrembleur, C.; Debuigne, A. Ethylene/Vinyl Acetate-Based Macrocycles via Organometallic-Mediated Radical Polymerization and CuAAC "Click" Reaction. Polym. Chem. 2018, 9, 273-278, 10.1039/C7PY01891F
Thomassin, J.-M.; Debuigne, A.; Jérôme, C.; Detrembleur, C. Design of Mesoporous Carbon Fibers from a Poly(acrylonitrile) Based Block Copolymer by a Simple Templating Compression Moulding Process. Polymer 2010, 51, 2965-2971, 10.1016/j.polymer.2010.05.010
Bryaskova, R.; Pencheva, D.; Kyulavska, M.; Bozukova, D.; Debuigne, A.; Detrembleur, C. Antibacterial Activity of Poly(vinyl Alcohol)-B-Poly(acrylonitrile) Based Micelles Loaded with Silver Nanoparticles. J. Colloid Interface Sci. 2010, 344, 424-428, 10.1016/j.jcis.2009.12.040
Egorova, K. S.; Ananikov, V. P. Toxicity of Metal Compounds: Knowledge and Myths. Organometallics 2017, 36, 4071-4090, 10.1021/acs.organomet.7b00605
Hurtgen, M.; Debuigne, A.; Mouithys-Mickalad, A.; Jérôme, R.; Jérôme, C.; Detrembleur, C. Synthesis of Poly(vinyl alcohol)/C60 and poly(N-vinylpyrrolidone)/C60 Nanohybrids as Potential Photodynamic Cancer Therapy Agents. Chem.-Asian J. 2010, 5, 859-868, 10.1002/asia.200900277
Drean, M.; Debuigne, A.; Goncalves, C.; Jerome, C.; Midoux, P.; Rieger, J.; Guegan, P. Use of Primary and Secondary Polyvinylamines for Efficient Gene Transfection. Biomacromolecules 2017, 18, 440-451, 10.1021/acs.biomac.6b01526
Dréan, M.; Debuigne, A.; Jérôme, C.; Goncalves, C.; Midoux, P.; Rieger, J.; Guégan, P. Poly(N-Methylvinylamine)-Based Copolymers for Improved Gene Transfection. Macromol. Biosci. 2018, 18, 1700353, 10.1002/mabi.201700353