Silicon Reagent with Functionalized Tetrafluoroethylene Fragments: Preparation and Coupling with Aldehydes

Journal of Organic Chemistry

Volumn 81, Issue 19, 2016, Pages 9455-9460

  Fedorov, Oleg V ^a   Struchkova, Marina I ^a   Dilman, Alexander D ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; FLUORINE CONTAINING POLYMERS; SILICON;

AZOMETHINES; BUILDING BLOCKES; C-C BOND FORMING; DIFLUOROCARBENE; FUNCTIONALIZED; POTASSIUM FLUORIDES; TETRAFLUOROETHYLENE; TRIMETHYLSILANE;

CHEMICAL REACTIONS;

ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; AZOMETHINE; BROMODIFLUOROMETHYLTRIMETHYLSILANE; CARBON; CYCLOPROPANE; DIFLUOROCARBENE; ETHYL BROMODIFLUOROACETATE; POTASSIUM FLUORIDE; REAGENT; SILANE DERIVATIVE; SILICON; TETRAFLUOROETHYLENE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; COVALENT BOND; CROSS COUPLING REACTION; CYCLOADDITION; NUCLEOPHILICITY; POLYMERIZATION; REACTION ANALYSIS; SILYLATION;

EID: 84990882856     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b01739     Document Type: Article

References (56)

1. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
2. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214-8264 10.1002/anie.201206566
3. Alonso, C.; de Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847-1935 10.1021/cr500368h
4. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786 10.1021/cr9408991
5. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683-730 10.1021/cr400473a
6. Uneyama, K. J. Fluorine Chem. 2008, 129, 550-576 10.1016/j.jfluchem.2008.05.012
7. Dilman, A. D.; Levin, V. V. Eur. J. Org. Chem. 2011, 2011, 831-841 10.1002/ejoc.201001558
8. Dilman, A. D.; Levin, V. V. Mendeleev Commun. 2015, 25, 239-244 10.1016/j.mencom.2015.07.001
9. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521 10.1021/cr1004293
10. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513-1522 10.1021/ar4003202
11. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 2012, 6679-6687 10.1002/ejoc.201200648
12. Wang, H.; Vicic, D. A. Synlett 2013, 24, 1887-1898 10.1055/s-0033-1339435
13. Toulgoat, F.; Langlois, B. R.; Medebielle, M.; Sanchez, J. Y. J. Org. Chem. 2007, 72, 9046-9052 10.1021/jo701318n
14. Petko, K. I.; Kot, S. Y.; Yagupolskii, L. M. J. Fluorine Chem. 2008, 129, 301-306 10.1016/j.jfluchem.2008.01.008
15. Chernykh, Y.; Hlat-Glembová, K.; Klepetářová, B.; Beier, P. Eur. J. Org. Chem. 2011, 2011, 4528-4531 10.1002/ejoc.201100667
16. Chernykh, Y.; Jurasek, B.; Beier, P. J. Fluorine Chem. 2015, 171, 162-168 10.1016/j.jfluchem.2014.08.004
17. Matoušek, V.; Václavík, J.; Hájek, P.; Charpentier, J.; Blastik, Z. E.; Pietrasiak, E.; Budinská, A.; Togni, A.; Beier, P. Chem.-Eur. J. 2016, 22, 417-424 10.1002/chem.201503531
18. O'Duill, M.; Dubost, E.; Pfeifer, L.; Gouverneur, V. Org. Lett. 2015, 17, 3466-3469 10.1021/acs.orglett.5b01510
19. Yudin, A. K.; Prakash, G. K. S.; Deffieux, D.; Bradley, M.; Bau, R.; Olah, G. A. J. Am. Chem. Soc. 1997, 119, 1572-1581 10.1021/ja962990n
20. Hagiwara, T.; Fuchikami, T. Chem. Lett. 1997, 26, 787-788 10.1246/cl.1997.787
21. Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145-153 10.1016/S0022-328X(00)81910-5
22. Chen, B.; Vicic, D. A. J. Fluorine Chem. 2014, 167, 139-142 10.1016/j.jfluchem.2014.06.023
23. Saijo, H.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2014, 136, 15158-15161 10.1021/ja5093776
24. Ohashi, M.; Shirataki, H.; Kikushima, K.; Ogoshi, S. J. Am. Chem. Soc. 2015, 137, 6496-6499 10.1021/jacs.5b03587
25. Konno, T.; Takano, S.; Takahashi, Y.; Konishi, H.; Tanaka, Y.; Ishihara, T. Synthesis 2011, 2011, 33-44 10.1055/s-0030-1258330
26. Linclau, B.; Boydell, A. J.; Timofte, R. S.; Brown, K. J.; Vinader, V.; Weymouth-Wilson, A. C. Org. Biomol. Chem. 2009, 7, 803-814 10.1039/b817260a
27. Dmowski, W. J. Fluorine Chem. 2012, 142, 6-13 10.1016/j.jfluchem.2012.06.018
28. Kirsch, P.; Bremer, M.; Huber, F.; Lannert, H.; Ruhl, A.; Lieb, M.; Wallmichrath, T. J. Am. Chem. Soc. 2001, 123, 5414-5417 10.1021/ja010024l
29. Kirsch, P.; Huber, F.; Lenges, M.; Taugerbeck, A. J. Fluorine Chem. 2001, 112, 69-72 10.1016/S0022-1139(01)00488-2
30. Kirsch, P.; Bremer, M. ChemPhysChem 2010, 11, 357-360 10.1002/cphc.200900745
31. Gatenyo, J.; Rozen, S. J. Fluorine Chem. 2009, 130, 332-335 10.1016/j.jfluchem.2008.12.009
32. York, C.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1994, 59, 6493-6494 10.1021/jo00100a068
33. Chang, Y.; Tewari, A.; Adi, A.-I.; Bae, C. Tetrahedron 2008, 64, 9837-9842 10.1016/j.tet.2008.08.009
34. Christy, M. E.; Colton, C. D.; Mackay, M.; Staas, W. H.; Wong, J. B.; Engelhardt, E. L.; Torchiana, M. L.; Stone, C. A. J. Med. Chem. 1977, 20, 421-430 10.1021/jm00213a021
35. Hu, M.; Ni, C.; Li, L.; Han, Y.; Hu, J. J. Am. Chem. Soc. 2015, 137, 14496-14501 10.1021/jacs.5b09888
36. Lee, C.-C.; Lin, S.-T.; Ke, S.-Y. Tetrahedron 2007, 63, 120-125 10.1016/j.tet.2006.10.041
37. Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2015, 17, 760-763 10.1021/acs.orglett.5b00097
38. Fedorov, O. V.; Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2015, 80, 5870-5876 10.1021/acs.joc.5b00904
39. Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. J. Org. Chem. 2012, 77, 5850-5855 10.1021/jo301094b
40. Levin, V. V.; Zemtsov, A. A.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2013, 15, 917-919 10.1021/ol400122k
41. Kosobokov, M. D.; Levin, V. V.; Zemtsov, A. A.; Struchkova, M. I.; Korlyukov, A. A.; Arkhipov, D. E.; Dilman, A. D. Org. Lett. 2014, 16, 1438-1441 10.1021/ol5002297
42. Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2014, 16, 3784-3787 10.1021/ol501674n
43. Levin, V. V.; Smirnov, V. O.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2015, 80, 9349-9353 10.1021/acs.joc.5b01590
44. Maslov, A. S.; Smirnov, V. O.; Struchkova, M. I.; Arkhipov, D. E.; Dilman, A. D. Tetrahedron Lett. 2015, 56, 5048-5050 10.1016/j.tetlet.2015.07.018
45. Trifonov, A. L.; Zemtsov, A. A.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2016, 18, 3458-3461 10.1021/acs.orglett.6b01641
46. Silyl ketene acetal 2 was previously isolated in only 12% yield, see: Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280 10.1016/S0040-4020(97)00683-2
47. Uneyama, K.; Mizutani, G. Chem. Commun. 1999, 613-614 10.1039/a900455f
48. Uneyama, K.; Mizutani, G.; Maeda, K.; Kato, T. J. Org. Chem. 1999, 64, 6717-6723 10.1021/jo990571d
49. Tsymbal, A. V.; Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2014, 79, 7831-7835 10.1021/jo501644m
50. Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071-1098 10.1021/cr010023b
51. Ni, C.; Hu, J. Synthesis 2014, 46, 842-863 10.1055/s-0033-1340856
52. Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390-12394 10.1002/anie.201306703
53. Wang, F.; Zhang, W.; Zhu, J.; Li, H.; Huang, K.-W.; Hu, J. Chem. Commun. 2011, 47, 2411-2413 10.1039/C0CC04548A
54. Levin, V. V.; Kozlov, M. A.; Song, Y.-H.; Dilman, A. D.; Belyakov, P. A.; Struchkova, M. I.; Tartakovsky, V. A. Tetrahedron Lett. 2008, 49, 3108-3111 10.1016/j.tetlet.2008.03.043
55. Yamada, S.; Noma, M.; Konno, T.; Ishihara, T.; Yamanaka, H. Org. Lett. 2006, 8, 843-845 10.1021/ol052897g
56. Yamada, S.; Noma, M.; Hondo, K.; Konno, T.; Ishihara, T. J. Org. Chem. 2008, 73, 522-528 10.1021/jo701975y