Stereospecific synthesis of tri- and tetrasubstituted α-fluoroacrylates by mizoroki-heck reaction

Organic Letters

Volumn 18, Issue 3, 2016, Pages 540-543

  Rousée, Kevin ^a   Bouillon, Jean Philippe ^a   Couve Bonnaire, Samuel ^a   Pannecoucke, Xavier ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; FLUORINATED HYDROCARBON; IODINATED HYDROCARBON; PALLADIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACRYLATES; CATALYSIS; HYDROCARBONS, FLUORINATED; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84957590828     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b03571     Document Type: Article

References (57)

1. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2013.
2. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
3. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308 10.1039/B711844A
4. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; John Wiley & Sons, Inc.: Hoboken, NJ, 2008.
5. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: Chichester, UK, 2009.
6. Handbook of Fluoropolymer Science and Technology; Smith, D. W.; Iacono, S. T.; Iyer, S. S., Eds; John Wiley & Sons, Inc.: Hoboken, NJ, 2014.
7. Cracowski, J.-M.; Montembault, V.; Bosc, D.; Ameduri, B.; Odobel, F.; Fontaine, L. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 1403 10.1002/pola.23249
8. Honda, H.; Sato, S.; Isomae, K.; Ookawa, J.; Kuwamura, T. (SS Pharmaceutical Co.) DE3407806, 1984.
9. Jaeger, E. P.; Jurs, P. C.; Stouch, T. R. E. Eur. J. Med. Chem. 1993, 28, 275 10.1016/0223-5234(93)90145-5
10. Hibi, S.; Kikuchi, K.; Yoshimura, H.; Nagai, M.; Tagami, K.; Abe, S.; Hishinuma, I.; Nagakawa, J.; Miyamoto, N. (Eisai Co., Ltd.), WO9613478, 1996.
11. Kaneko, T.; Clark, R.; Ohi, N.; Ozaki, F.; Kawahara, T.; Kamada, A.; Okano, K.; Yokohama, H.; Muramoto, K.; Arai, T.; Ohkuro, M.; Takenaka, O.; Sonoda, J. (Eisai Co., Ltd.) WO9806720, 1998.
12. Wiedeman, P. E.; Djuric, S. W.; Pilushchev, M.; Sciotti, R. J.; Madar, D. J.; Kopecka, H. US20020115669(A1), 2002.
13. Sun, J.; Yang, Y.; Huang, Y. (Chengdu Inst Biology CAS), CN103254053(A), 2013.
14. Pierry, C.; Couve-Bonnaire, S.; Guilhaudis, L.; Neveu, C.; Marotte, A.; Lefranc, B.; Cahard, D.; Ségalas-Milazzo, I.; Leprince, J.; Pannecoucke, X. ChemBioChem 2013, 14, 1620 10.1002/cbic.201300325
15. Dutheuil, G.; Pierry, C.; Villiers, E.; Couve-Bonnaire, S.; Pannecoucke, X. New J. Chem. 2013, 37, 1320 10.1039/C2NJ40891K
16. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291 10.1016/0040-4020(95)00912-R
17. Van der Veken, P.; Senten, K.; Kertesz, I.; De Meester, I.; Lambeir, A.-M.; Maes, M.-B.; Scharpé, S.; Haemers, L. A.; Augustyns, K. J. Med. Chem. 2005, 48, 1768 10.1021/jm0495982
18. Chang, W.; Mosley, R. T.; Bansal, S.; Keilman, M.; Lam, A. M.; Furman, P. A.; Otto, M. J.; Sofia, M. J. Bioorg. Med. Chem. Lett. 2012, 22, 2938 10.1016/j.bmcl.2012.02.051
19. Landelle, G.; Bergeron, M.; Turcotte-Savard, M. O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867 10.1039/c0cs00201a
20. Yanai, H.; Taguchi, T. Eur. J. Org. Chem. 2011, 2011, 5939 10.1002/ejoc.201100495
21. Zoute, L.; Dutheuil, G.; Quirion, J.-C.; Jubault, P.; Pannecoucke, X. Synthesis 2006, 2006, 3409 10.1055/s-2006-950208
22. Moghadam, G. E.; Penne, J. S. Bull. Soc. Chim. Fr. 1985, 448
23. Sano, S.; Kuroda, Y.; Saito, K.; Ose, Y.; Nagao, Y. Tetrahedron 2006, 62, 11881 10.1016/j.tet.2006.09.096
24. Larnaud, F.; Pfund, E.; Linclau, B.; Lequeux, T. Tetrahedron 2014, 70, 5632 and references cited therein 10.1016/j.tet.2014.06.081
25. Lemonnier, G.; Zoute, L.; Dupas, G.; Quirion, J.-C.; Jubault, P. J. Org. Chem. 2009, 74, 4124 10.1021/jo900422m
26. Satoh, T.; Itoh, N.; Onda, K.-I.; Kitoh, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2800 10.1246/bcsj.65.2800
27. Yoshimatsu, M.; Murase, Y.; Itoh, A.; Tanabe, G.; Muraoka, O. Chem. Lett. 2005, 34, 998 10.1246/cl.2005.998
28. Qian, J.; Yi, W.; Lv, M.; Cai, C. Synlett 2014, 26, 127 10.1055/s-0034-1378917
29. Barma, D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. J. Am. Chem. Soc. 2003, 125, 3218 10.1021/ja029938d
30. Augustine, J. K.; Bombrun, A.; Venkatachaliah, S.; Jothi, A. Org. Biomol. Chem. 2013, 11, 8065 10.1039/c3ob41592a
31. Schneider, C.; Masi, D.; Couve-Bonnaire, S.; Pannecoucke, X.; Hoarau, C. Angew. Chem., Int. Ed. 2013, 52, 3246 10.1002/anie.201209446
32. Rousée, K.; Schneider, C.; Couve-Bonnaire, S.; Pannecoucke, X.; Levacher, V.; Hoarau, C. Chem.-Eur. J. 2014, 20, 15000 10.1002/chem.201405119
33. Rousée, K.; Schneider, C.; Bouillon, J.-P.; Levacher, V.; Hoarau, C.; Couve-Bonnaire, S.; Pannecoucke, X. Org. Biomol. Chem. 2016, 14, 353 10.1039/C5OB02213D
34. Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions and More, 1 st ed.; de Meijere, A.; Bräse, S.; Oestreich, M., Eds.; Wiley-VCH: Weinheim, 2014; Vol. 2, pp 533-663.
35. The Mizoroki-Heck Reaction; Oestreich, M., Ed.; John Wiley & Sons, Ltd: Chichester, UK, 2009.
36. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009 10.1021/cr9903048
37. Taracido, I. C.; Harrington, E. M.; Hersperger, R.; Lattmann, R.; Miltz, W.; Weigand, K. (Novartis Institutes for Biomedical Research) US20090291942(A1), 2009.
38. Patrick, T. B.; Agboka, T. Y.; Gorrell, K. J. Fluorine Chem. 2008, 129, 983 10.1016/j.jfluchem.2008.02.006
39. Hirotaki, K.; Hanamoto, T. J. Org. Chem. 2011, 76, 8564 10.1021/jo201720x
40. Li, Y.; Tu, D.-H.; Gu, Y.-J.; Wang, B.; Wang, Y.-Y.; Liu, Z.-T.; Liu, Z.-W.; Lu, J. Eur. J. Org. Chem. 2015, 2015, 4340 10.1002/ejoc.201500597
41. Ohff, M.; Ohff, A.; Van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687 10.1021/ja9729692
42. Shaw, B. L. New J. Chem. 1998, 22, 77 10.1039/a709028e
43. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem.-Eur. J. 2001, 7, 1703 10.1002/1521-3765(20010417)7:8<1703::AID-CHEM17030>3.0.CO;2-K
44. Yao, Q.; Kinney, E. P.; Yang, Z. J. Org. Chem. 2003, 68, 7528 10.1021/jo034646w
45. Moreno-Mañas, M.; Perez, M.; Pleixats, R. Tetrahedron Lett. 1996, 37, 7449 10.1016/0040-4039(96)01608-5
46. Gürtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107 10.1002/(SICI)1521-3765(19991105)5:11<3107::AID-CHEM3107>3.0.CO;2-#
47. Calo, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. J. Org. Chem. 2003, 68, 2929 10.1021/jo026877t
48. Calo, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Angew. Chem., Int. Ed. 2009, 48, 6101 10.1002/anie.200902337
49. Gottumukkala, A. L.; de Vries, J. G.; Minnaard, A. J. Chem.-Eur. J. 2011, 17, 3091 10.1002/chem.201003643
50. Xu, D.; Lu, C.; Chen, W. Tetrahedron 2012, 68, 1466 10.1016/j.tet.2011.12.017
51. Lee, H. S.; Kim, K. H.; Kim, S. H.; Kim, J. N. Adv. Synth. Catal. 2012, 354, 2419 10.1002/adsc.201200306
52. He, Z.; Kirchberg, S.; Frohlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699 10.1002/anie.201108211
53. He, Z.; Wibbeling, B.; Studer, A. Adv. Synth. Catal. 2013, 355, 3639 10.1002/adsc.201300846
54. Gigant, N.; Quintin, F.; Bäckvall, J. E. J. Org. Chem. 2015, 80, 2796 10.1021/acs.joc.5b00148
55. Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Org. Biomol. Chem. 2007, 5, 1151 and references therein 10.1039/b701559c
56. Singh, A. K.; Parthsarthy, R.; Lohani, M. J. Chem. Pharm. Res. 2012, 4, 779
57. Chinnaiyan, A. M.; Lnu, S.; Cao, Q. (The Regents of the University of Michigan) WO2011103016(A2), 2011.