Visible-light hypervalent iodide carboxylate photo(trifluoro)methylations and controlled radical polymerization of fluorinated alkenes

Angewandte Chemie - International Edition

Volumn 52, Issue 38, 2013, Pages 10027-10030

  Asandei, Alexandru D ^a   Adebolu, Olumide I ^a   Simpson, Christopher P ^a   Kim, Joon Sung ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

block copolymers; hypervalent iodine carboxylates; polymerization; trifluoromethylation; vinylidene fluorides

Indexed keywords

BLOCK COPOLYMER SYNTHESIS; CHAIN TRANSFER AGENTS; CONTROLLED RADICAL POLYMERIZATION; HYPERVALENT IODINE; PHOTOINITIATORS; TRIFLUOROMETHYLATION; VINYLIDENE FLUORIDE; VISIBLE LIGHT;

ALKYLATION; ATOM TRANSFER RADICAL POLYMERIZATION; BLOCK COPOLYMERS; CARBOXYLATION; HYDROCARBONS; IODINE; METHYLATION; POLYMERIZATION;

FREE RADICAL POLYMERIZATION;

ALKENE; CARBOXYLIC ACID; IODIDE;

ARTICLE; BLOCK COPOLYMERS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; HYPERVALENT IODINE CARBOXYLATES; METHYLATION; POLYMERIZATION; TRIFLUOROMETHYLATION; VINYLIDENE FLUORIDES;

BLOCK COPOLYMERS; HYPERVALENT IODINE CARBOXYLATES; POLYMERIZATION; TRIFLUOROMETHYLATION; VINYLIDENE FLUORIDES;

ALKENES; CARBOXYLIC ACIDS; CATALYSIS; HALOGENATION; IODIDES; METHYLATION; MOLECULAR STRUCTURE; POLYMERIZATION;

EID: 84884254853     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303826     Document Type: Article

References (49)

1. M. A. McClinton, D. A. McClinton, Tetrahedron 1992, 48, 6555.
2. J. A. Ma, D. J. Cahard, J. Fluorine Chem. 2007, 128, 975.
3. T. Besset, C. Schneider, D. Cahard, Angew. Chem. 2012, 124, 5134
4. Angew. Chem. Int. Ed. 2012, 51, 5048.
5. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470.
6. X.-F. Wu, H. Neumann, M. R. Beller, Chem. Asian J. 2012, 7, 1744.
7. S. Roy, B. T. Gregg, G. W. Gribble, V. D. Le, S. Roy, Tetrahedron 2011, 67, 2161.
8. G. K. S. Prakash, P. V. Jog, T. D. Patrice, P. T. D. Batamack, G. A. Olah, Science 2012, 338, 1324.
9. E. Mejía, A. Togni, ACS Catal. 2012, 2, 521.
10. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475.
11. A. Studer, Angew. Chem. 2012, 124, 9082
12. Angew. Chem. Int. Ed. 2012, 51, 8950.
13. S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, V. Gouverneur, J. Am. Chem. Soc. 2013, 135, 2505.
14. C.-J. Wallentin, J. D. Nguyen, P. Finkbeiner, R. J. Corey, C. R. J. Stephenson, J. Am. Chem. Soc. 2012, 134, 8875.
15. M. G. Dhara, S. Banerjee, Prog. Polym. Sci. 2010, 35, 1022.
16. B. Ameduri, Chem. Rev. 2009, 109, 6632.
17. B. Ameduri, B. Boutevin, Well Architectured Fluoropolymers: Synthesis Properties and Applications, Elsevier, Amsterdam 2004, pp. 1-99.
18. W. A. Braunecker, K. Matyjaszewski, Prog. Polym. Sci. 2007, 32, 93.
19. A. Goto, T. Fukuda, Prog. Polym. Sci. 2004, 29, 329.
20. A. D. Asandei, O. I. Adebolu, C. P. Simpson, J. Am. Chem. Soc. 2012, 134, 6080.
21. M. Oka, M. Tatemoto, Contemporary Topics in Polymer Science, Vol.4, Plenum, New York, 1984, p. 763.
22. G. David, C. Boyer, J. Tonnar, B. Ameduri, P. Lacroix-Desmazes, B. Boutevin, Chem. Rev. 2006, 106, 3936.
23. A. D. Asandei, C. P. Simpson, O. I. Adebolu, ACS Symp. Ser. 2012, 1106, 47.
24. S. Yamago, Y. Nakamura, Polymer 2013, 54, 981-994.
25. P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123.
26. P. J. Stang, V. V. Zhdankin, Chem. Rev. 2002, 102, 2523.
27. P. J. Stang, V. V. Zhdankin, Chem. Rev. 2008, 108, 5299.
28. H. Togo, M. Katohgia, Synlett 2001, 565.
29. H. Suginome, CRC Handbook of Organic Photochemistry and Photobiology, CRC, Boca Raton, 2004, pp. 109 -1- 44.
30. J. L. Courtneidge, J. Lusztyk, D. Page, Tetrahedron Lett. 1994, 35, 1003.
31. J. Madsen, C. Viuf, M. Bols, Chem. Eur. J. 2000, 6, 1140.
32. A. Alberti, M. Benaglia, Res. Chem. Intermed. 1989, 11, 117.
33. T. Kitamura, CRC Handbook of Organic Photochemistry and Photobiology, CRC, Boca Raton, 2004, pp. 110 -1- 11.
34. L. M. Richards, U.S. Patent 2,467,231, 1949.
35. G. S. Georgiev, Polym. Bull. 1999, 43, 223.
36. H. Han, N. V. Tsarevsky, Polym. Chem. 2012, 3, 1910.
37. R. Kopitzky, H. Willner, A. Hermann, H. Oberhammer, Inorg. Chem. 2001, 40, 2693.
38. T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527.
39. W. D. Johnson, J. E. Sherwood, Aust. J. Chem. 1971, 24, 2281.
40. R. Kaptein, J. Brokken-Zijp, F. J. J. deKanter, J. Am. Chem. Soc. 1972, 94, 6280.
41. V. D. Filimonov, O. K. Poleshchuk, E. A. Krasnokutskaya, G. Frenking, J. Mol. Model. 2011, 17, 2759.
42. P. Lacroix-Desmazes, J. Tonnar, B. Boutevin, Macromol. Symp. 2007, 248, 150.
43. H. Gottam, T. K. J. Vinod, Org. Chem. 2011, 76, 974.
44. J. Gallos, A. J. Varvoglis, Chem. Soc. Perkin Trans. 1 1983, 1999.
45. M. R. Britten-Kelley, A. Goosen, A. Scheffer, J. South African Chem. Inst. 1975, 28, 224.
46. F. Fontana, F. Minisci, M. C. N. Barbosa, E. Vismara, Gazz. Chim. Ital. 1992, 122, 167.
47. P. Gray, A. A. Herod, A. Jones, Chem. Rev. 1971, 71, 247.
48. J. A. LaVerne, L. Wojnarovits, J. Phys. Chem. 1994, 98, 12635.
49. M. Hauptschein, R. E. Oesterling, M. Braid, E. A. Tyczkowski, D. M. Gardner, J. Org. Chem. 1963, 28, 1281.