Geminal silicon/zinc reagent as an equivalent of difluoromethylene bis-carbanion

Organic Letters

Volumn 16, Issue 5, 2014, Pages 1438-1441

  Kosobokov, Mikhail D ^a   Levin, Vitalij V ^a   Zemtsov, Artem A ^a   Struchkova, Marina I ^a   Korlyukov, Alexander A ^b   Arkhipov, Dmitry E ^b   Dilman, Alexander D ^a  

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

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896744493     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5002297     Document Type: Article

References (41)

1. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; John Wiley & Sons: Chichester, 2009.
2. Begue, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley-VCH: Weinheim, 2008.
3. O'Hagan, D.; S. Rzepa, H. Chem. Commun. 1997, 645-652
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
5. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
6. O'Hagan, D. J. Fluorine Chem. 2010, 131, 1071-1081
7. Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303-319
8. Blackburn, G. M.; England, D. A.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 930-932
9. Hakogi, T.; Yamamoto, T.; Fujii, S.; Ikeda, K.; Katsumura, S. Tetrahedron Lett. 2006, 47, 2627-2630
10. Xu, Y.; Aoki, J.; Shimizu, K.; Umezu-Goto, M.; Hama, K.; Takanezawa, Y.; Yu, S.; Mills, G. B.; Arai, H.; Qian, L.; Prestwich, G. D. J. Med. Chem. 2005, 48, 3319-3327
11. Meanwell, N. A. J. Med. Chem. 2011, 54, 2529-2591
12. Al-Maharik, N.; O'Hagan, D. Aldrichimica Acta 2011, 44, 65-75
13. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683
14. Qing, F.-L.; Zheng, F. Synlett 2011, 1052-1072
15. gem -Difluorocyclopropanes constitute a specific class, which is generally accessed by difluorocarbene addition; see: Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071-1098
16. Levin, V. V.; Zemtsov, A. A.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2013, 15, 917-919
17. Zemtsov, A. A.; Kondratyev, N. S.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2014, 79, 818-822
18. Prakash, G. K. S.; Hu, J.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2003, 42, 5216-5219
19. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930
20. Beier, P.; Alexandrova, A. V.; Zibinsky, M.; Surya Prakash, G. K. Tetrahedron 2008, 64, 10977-10985
21. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786
22. Yudin, A. K.; Prakash, G. K. S.; Deffieux, D.; Bradley, M.; Bau, R.; Olah, G. A. J. Am. Chem. Soc. 1997, 119, 1572-1581
23. 2C(=NR)-, see: Kobayashi, T.; Nakagawa, T.; Amii, H.; Uneyama, K. Org. Lett. 2003, 5, 4297-4300
24. Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145-153
25. Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. J. Org. Chem. 2012, 77, 5850-5855
26. Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390-12394
27. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040-6044
28. Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107-1110
29. Jones, P.; Reddy, C. K.; Knochel, P. Tetrahedron 1998, 54, 1471-1490
30. Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. Tetrahedron Lett. 1999, 40, 33-36
31. Hatakeyama, T.; Nakagawa, N.; Nakamura, M. Org. Lett. 2009, 11, 4496-4499
32. Stadtmüller, H.; Lentz, R.; Tucker, C. E.; Stuedemann, T.; Doerner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027-7028
33. Stadtmüller, H.; Vaupel, A.; Tucker, C. E.; Stüdemann, T.; Knochel, P. Chem.-Eur. J. 1996, 2, 1204-1220
34. Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 5743-5753
35. Melzig, L.; Diene, C. R.; Rohbogner, C. J.; Knochel, P. Org. Lett. 2011, 13, 3174-3177
36. Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435-1462
37. Gosmini, C.; Bégouin, J.-M.; Moncomble, A. Chem. Commun. 2008, 3221-3233
38. fI to give Co(III) species are known; see: Harrison, D. J.; Gorelsky, S. I.; Lee, G. M.; Korobkov, I.; Baker, R. T. Organometallics 2013, 32, 12-15 and reference cited therein
39. Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286-9289
40. Burton, D. J.; Hartgraves, G. A. J. Fluorine Chem. 2007, 128, 1198-1215
41. Mogi, R.; Morisaki, K.; Hu, J.; Prakash, G. K. S.; Olah, G. A. J. Fluorine Chem. 2007, 128, 1098-1103