Reactions of difluorocarbene with organozinc reagents

Organic Letters

Volumn 15, Issue 4, 2013, Pages 917-919

  Levin, Vitalij V ^a   Zemtsov, Artem A ^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

BROMINE; DIFLUOROCARBENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

BROMINE; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, FLUORINATED; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 84873967689     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400122k     Document Type: Article

References (53)

1. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
3. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Blackwell: Oxford, U.K., 2009.
4. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950-8958
5. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 6679-6687
6. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470-477
7. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
8. Dilman, A. D.; Levin, V. V. Eur. J. Org. Chem. 2011, 831-841
9. Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867-2908
10. Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2010, 6, 65
11. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975-996
12. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786
13. 2-containing compounds, see: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683
14. 2Br fragments, see: Zhao, Y.; Gao, B.; Hu, J. J. Am. Chem. Soc. 2012, 134, 5790-5793
15. Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494-1497
16. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 5524-5527
17. Prakash, G. K. S.; Ganesh, S. K.; Jones, J.-P.; Kulkarni, A.; Masood, K.; Swabeck, J. K.; Olah, G. A. Angew. Chem., Int. Ed. 2012, 51, 12090-12094
18. Shen, X.; Zhang, W.; Ni, C.; Gu, Y.; Hu, J. J. Am. Chem. Soc. 2012, 134, 16999-17002
19. Wu, J.; Cao, S.; Liu, N.; Shen, L.; Yu, J.; Zhang, J.; Li, H.; Qian, X. Org. Biomol. Chem. 2010, 8, 2386-2391
20. Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560-5563
21. Liu, G.; Wang, X.; Lu, X.; Xu, X.-H.; Tokunaga, E.; Shibata, N. ChemistryOpen 2012, 1, 227-231
22. For a review on difluorocyclopropanation, see: Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071-1098
23. Hudlicky, M. Org. React. 1988, 35, 513-637
24. Singh, R. P.; Shreeve, J. M. Synthesis 2002, 2561-2578
25. Singh, R. P.; Meshri, D. T.; Shreeve, J. M. In Advances in Organic Synthesis: Modern Organofluorine Chemistry-Synthetic Aspects; Atta-Ur-Rahman, Laali, K. K., Eds.; Bentham Science Publishers Ltd.: Hilversum, The Netherlands, 2006; Vol. 2, pp 291-326.
26. Qing, F.-L.; Zheng, F. Synlett 2011, 1052-1072
27. Brahms, D. L. S.; Dailey, W. P. Chem. Rev. 1996, 96, 1585-1632
28. Moss, R. A.; Wang, L.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2009, 131, 2128-2130
29. Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009, 11, 2109-2112
30. Sperry, J. B.; Sutherland, K. Org. Process Res. Dev. 2011, 15, 721-725
31. Wang, F.; Huang, W.; Hu, J. Chin. J. Chem. 2011, 29, 2717-2721
32. Ando, M.; Wada, T.; Sato, N. Org. Lett. 2006, 8, 3805-3808
33. Rico, I.; Cantacuzene, D.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1982, 1063-1065
34. Xu, B.; Mae, M.; Hong, J. A.; Li, Y.; Hammond, G. B. Synthesis 2006, 803-806
35. Everett, T. S.; Purrington, S. T.; Bumgardner, C. L. J. Org. Chem. 1984, 49, 3702-3706
36. Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641-1716
37. Burton, D. J.; Wiemers, D. M. J. Fluorine Chem. 1981, 18, 573-582
38. Mikami, K.; Tomita, Y.; Itoh, Y. Angew. Chem., Int. Ed. 2010, 49, 3819-3822
39. For a review, see: Marek, I. Tetrahedron 2002, 58, 9463-9475
40. Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189-275
41. Burton, D. J.; Lu, L. Top. Curr. Chem. 1997, 193, 45-89
42. Dolbier, W. R., Jr.; Tian, F.; Duan, J.-X.; Li, A.-R.; Ait-Mohand, S.; Bautista, O.; Buathong, S.; Marshall Baker, J.; Crawford, J.; Anselme, P.; Cai, X. H.; Modzelewska, A.; Koroniak, H.; Battiste, M. A.; Chen, Q.-Y. J. Fluorine Chem. 2004, 125, 459-469
43. Burton, D. J.; Naae, D. G. J. Am. Chem. Soc. 1973, 95, 8467-8468
44. Dolbier, W. R.; Wojtowicz, H.; Burkholder, C. R. J. Org. Chem. 1990, 55, 5420-5422
45. Seyferth, D.; Hopper, S. P.; Darragh, K. V. J. Am. Chem. Soc. 1969, 91, 6536-6537
46. Oshiro, K.; Morimoto, Y.; Amii, H. Synthesis 2010, 2080-2084
47. Birchall, J. M.; Cross, G. E.; Haszeldine, R. N. Proc. Chem. Soc. 1960, 81
48. Wang, F.; Zhang, L.; Zheng, J.; Hu, J. J. Fluorine Chem. 2011, 132, 521-528
49. Wang, F.; Luo, T.; Hu, J.; Wang, Y.; Krishnan, H. S.; Jog, P. V.; Ganesh, S. K.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. 2011, 50, 7153-7157
50. Wang, F.; Zhang, W.; Zhu, J.; Li, H.; Huang, K.-W.; Hu, J. Chem. Commun. 2011, 47, 2411-2413
51. Yudin, A. K.; Prakash, G. K. S.; Deffieux, D.; Bradley, M.; Bau, R.; Olah, G. A. J. Am. Chem. Soc. 1997, 119, 1572-1581
52. Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. J. Org. Chem. 2012, 77, 5850-5855
53. Lithium chloride may affect the reactivity of organozinc species. See: Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107-1110