Living radical polymerization via organic superbase catalysis

Polymers

Volumn 6, Issue 3, 2014, Pages 860-872

  Lei, Lin ^a   Tanishima, Miho ^a   Goto, Atsushi ^a   Kaji, Hironori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkyl iodide; Living radical polymerization; Organic catalysts; Organic superbases; Radical chemistry; Reversible complexation mediated polymerization

Indexed keywords

ACRYLIC MONOMERS; CATALYSTS; ESTERS; STYRENE;

ALKYL IODIDES; LIVING RADICAL POLYMERIZATION; ORGANIC CATALYSTS; RADICAL CHEMISTRY; REVERSIBLE COMPLEXATION; SUPERBASES;

LIVING POLYMERIZATION;

EID: 84899526090     PISSN: None     EISSN: 20734360     Source Type: Journal    
DOI: 10.3390/polym6030860     Document Type: Article

References (41)

1. Mukherjee, S.; Yang, J.W.; Hoffmann, S.; List, B. Asymmetric Enamine Catalysis. Chem. Rev. 2007, 107, 5471-5569.
2. Hegedus, L.S. Organocatalysts in Organic Synthesis. J. Am. Chem. Soc. 2009, 131, 17995-17997.
3. Zhong, C.; Shi, X. When Organocatalysis Meets Transition-Metal Catalysis. Eur. J. Org. Chem. 2010, 2010, 2999-3025.
4. Grasa, G.A.; Singh, R.; Nolan, S.P. Transesterification/Acylation Reactions Catalyzed by Molecular Catalysts. Synthesis 2004, 2004, 971-985.
5. Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Guanidine-Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction. Adv. Synth. Catal. 2005, 347, 1643-1648.
6. Ishikawa, T.; Kumamoto, T. Guanidines in Organic Synthesis. Synthesis 2006, 2006, 737-752.
7. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Asymmetric Aminocatalysis-Gold Rush in Organic Chemistry. Angew. Chem. Int. Ed. 2008, 47, 6138-6171.
8. Lohmeijer, B.G.G.; Pratt, R.C.; Leibfarth, F.; Logan, J.W.; Long, D.A.; Dove, A.P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R.M.; Hedrick J.L. Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters. Macromolecules 2006, 39, 8574-8583.
9. Kakuchi, T.; Chen, Y.; Kitakado, J.; Mori, K.; Fuchise, K.; Satoh, T. Organic Superbase as an Efficient Catalyst for Group Transfer Polymerization of Methyl Methacrylate. Macromolecules 2011, 44, 4641-4647.
10. Tsarevsky, N.V.; Sumerlin, B.S. Fundamentals of Controlled/Living Radical Polymerization, 1st ed.; Royal Society of Chemistry: London, UK, 2013.
11. Matyjaszewski, K.; Möller, M. Polymer Science: A Comprehensive Reference, 1st ed.; Elsevier: Amsterdam, the Netherlands, 2012.
12. Moad, G.; Solomon, D.H. The Chemistry of Radical Polymerization, 2nd ed.; Elsevier: Amsterdam, the Netherlands, 2006.
13. Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Nitroxide-mediated polymerization. Prog. Polym. Sci. 2013, 38, 63-235.
14. Matyjaszewski, K. Atom transfer radical polymerization (ATRP): Current status and future perspectives. Macromolecules 2012, 45, 4015-4039.
15. Ouchi, M.; Terashima, T.; Sawamoto, M. Transition metal-catalyzed living radical polymerization: Toward perfection in catalysis and precision polymer synthesis. Chem. Rev. 2009, 109, 4963-5050.
16. Lena, F.; Matyjaszewski, K. Transition metal catalysts for controlled radical polymerization. Prog. Polym. Sci., 2010, 35, 959-1021.
17. Moad, G.; Rizzardo, E.; Thang, S.H. Living radical polymerization by the RAFT process-A second update. Aust. J. Chem. 2009, 62, 1402-1472.
18. Keddie, D.J.; Moad, G.; Rizzado, E.; Thang, S.H. RAFT agent design and synthesis. Macromolecules 2012, 45, 5321-5342.
19. David, G.; Boyer, C.; Tonnar, J.; Ameduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Use of iodocompounds in radical polymerization. Chem. Rev. 2006, 106, 3936-3962.
20. Yamago, S. Precision polymer synthesis by degenerative transfer controlled/living radical polymerization using organotellurium, organostibine and organobismuthine chain-transfer agents. Chem. Rev. 2009, 109, 5051-5068.
21. Fukuda, T. Fundamental kinetic aspects of living radical polymerization and the use of gel permeation chromatography to shed light on them. J. Polym. Sci. A Polym. Chem. 2004, 42, 4743-4755.
22. Fischer, H. The persistent radical effect: A principle for selective radical reactions and living radical polymerizations. Chem. Rev. 2001, 101, 3581-3618.
23. Goto, A.; Fukuda, T. Kinetics of living radical polymerization. Prog. Polym. Sci. 2004, 29, 329-385.
24. Fukuda, T.; Goto, A. Controlled and Living Radical Polymerization-Principles and Fundamentals. In Polymer Science: A Comprehensive Reference, 1st ed.; Matyjaszewski, K., Möller, M., Eds.; Elsevier: Amsterdam, the Netherlands, 2012; pp. 120-157.
25. Goto, A.; Zushi, H.; Hirai, N.; Wakada, T.; Tsujii, Y.; Fukuda, T. Living radical polymerizations with germanium, tin and phosphorus catalysts-Reversible chain transfer catalyzed polymerizations (RTCPs). J. Am. Chem. Soc. 2007, 129, 13347-13354.
26. Goto, A.; Hirai, N.; Wakada, T.; Nagasawa, K.; Tsujii, Y.; Fukuda, T. Living radical polymerization with nitrogen catalyst: Reversible chain transfer catalyzed polymerization with N-iodosuccinimide. Macromolecules 2008, 41, 6261-6264.
27. Goto, A.; Hirai, N.; Nagasawa, K.; Tsujii, Y.; Fukuda, T.; Kaji, H. Phenols and carbon compounds as efficient organic catalysts for reversible chain transfer catalyzed living radical polymerization (RTCP). Macromolecules 2010, 43, 7971-7978.
28. Vana, P.; Goto, A. Kinetic simulations of reversible chain transfer catalyzed polymerization (RTCP): Guidelines to optimum molecular weight control. Macromol. Theory Simul. 2010, 19, 24-35.
29. Yorizane, M.; Nagasuga, T.; Kitayama, Y.; Tanaka, A.; Minami, H.; Goto, A.; Fukuda, T.; Okubo, M. Reversible chain transfer catalyzed polymerization (RTCP) of methyl methacrylate with nitrogen catalyst in an aqueous microsuspension system. Macromolecules 2010, 43, 8703-8705.
30. Goto, A.; Tsujii, Y.; Fukuda, T. Reversible chain transfer catalyzed polymerization (RTCP): A new class of living radical polymerization. Polymer 2008, 49, 5177-5185.
31. Goto, A.; Tsujii, Y.; Kaji, H. Living Radical Polymerizations with Organic Catalysts. In Fundamentals of Controlled/Living Radical Polymerization, 1st ed.; Tsarevsky, N.V., Sumerlin, B.S., Eds.; Royal Society of Chemistry: London, UK, 2013; pp. 250-286.
32. Goto, A.; Suzuki, T.; Ohfuji, H.; Tanishima, M.; Fukuda, T.; Tsujii, Y.; Kaji, H. Reversible Complexation Mediated Living Radical Polymerization (RCMP) using organic catalysts. Macromolecules 2011, 44, 8709-8715.
33. Goto, A.; Tsujii, Y.; Kaji, H. Reversible Complexation Mediated Polymerization (RCMP) of Methyl Methacrylate. ACS Symp. Ser. 2012, 1100, 305-315.
34. Ohtsuki, A.; Goto, A.; Kaji, H. Visible-Light-Induced reversible complexation mediated living radical polymerization of methacrylates with organic catalysts. Macromolecules 2013, 46, 96-102.
35. Goto, A.; Ohtsuki A.; Ohfuji, H.; Tanishima, M.; Kaji, H. Reversible generation of a carbon-centered radical from alkyl iodide using organic salts and their application as organic catalysts in living radical polymerization. J. Am. Chem. Soc. 2013, 135, 11131-11139.
36. Moad, G.; Rizzardo, E. Alkoxyamine-Initiated Living Radical Polymerization: Factors Affecting Alkoxyamine Homolysis Rate. Macromolecules 1995, 28, 8722-8728.
37. Goto, A.; Fukuda, T. Determination of the activation rate constants of alkyl halide initiators for atom transfer radical polymerization. Macromol. Rapid Commun. 1999, 20, 633-636.
38. Schulte, T.; Studer, A. New Seven-and Eight-Membered Cyclic Alkoxyamines for the Living Free Radical Polymerization. Macromolecules 2003, 36, 3078-3084.
39. Ishikawa, T. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts; John Wiley & Sons: London, UK, 2009.
40. Lacroix-Desmazes, P.; Severac, R.; Boutevin, B. Reverse iodine transfer polymerization of methyl acrylate and n-butyl acrylate. Macromolecules 2005, 38, 6299-6309.
41. Tonnar, P.; Lacroix-Desmazes, P. Use of sodium iodide as the precursor to the control agent in ab initio emulsion polymerization. Angew. Chem. Int. Ed. 2008, 47, 1294-1297.