Oxidative heck arylation for the stereoselective synthesis of tetrasubstituted olefins using nitroxides as oxidants

Angewandte Chemie - International Edition

Volumn 51, Issue 15, 2012, Pages 3699-3702

  He, Zhiheng ^a   Kirchberg, Sylvia ^a   Fröhlich, Roland ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

alkenes; boronic acids; C H arylation; palladium; TEMPO

Indexed keywords

ARYLATIONS; BORONIC ACID; C-H ARYLATION; DIOXYGENS; HECK ARYLATION; METHYL ACRYLATES; NITROXIDES; ROOM TEMPERATURE; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; TEMPO; TETRASUBSTITUTED OLEFINS;

AROMATIC COMPOUNDS; NITROGEN OXIDES; OLEFINS; OXIDANTS; PALLADIUM; STEREOCHEMISTRY; STEREOSELECTIVITY;

CHEMICAL REACTIONS;

EID: 84859524880     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108211     Document Type: Article

References (53)

1. R. F. Heck, Org. React. 1982, 27, 345
2. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009
3. M. Oestreich, The Mizoroki-Heck Reaction, Wiley, Chichester, 2009
4. V. Coeffard, P. J. Guiry, Curr. Org. Chem. 2010, 14, 212
5. J. Ruan, J. Xiao, Acc. Chem. Res. 2011, 44, 614
6. D. Mc Cartney, P. J. Guiry, Chem. Soc. Rev. 2011, 40, 5122.
7. B. Karimi, H. Behzadnia, D. Elhamifar, P. F. Akhavan, F. K. Esfahani, A. Zamani, Synthesis 2010, 1399.
8. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313
9. J. P. Parrish, Y. C. Jung, S. I. Shin, K. W. Jung, J. Org. Chem. 2002, 67, 7127
10. Y. C. Jung, R. K. Mishra, C. H. Yoon, K. W. Jung, Org. Lett. 2003, 5, 2231
11. M. M. S. Andappan, P. Nilsson, H. von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212
12. K. S. Yoo, C. H. Yoon, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384
13. J. Lindh, P. Enquist, A. Pilotti, P. Nilsson, M. Larhed, J. Org. Chem. 2007, 72, 7957
14. J. H. Delcamp, A. P. Brucks, M. C. White, J. Am. Chem. Soc. 2008, 130, 11270
15. E. W. Werner, M. S. Sigman, J. Am. Chem. Soc. 2010, 132, 13981
16. Y. Liu, D. Li, C.-M. Park, Angew. Chem. 2011, 123, 7471
17. Angew. Chem. Int. Ed. 2011, 50, 7333.
18. K. Itami, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2003, 125, 14670
19. C. Zhou, R. C. Larock, J. Org. Chem. 2005, 70, 3765
20. M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc. 2005, 127, 12506
21. Z. Tan, E.-i. Negishi, Angew. Chem. 2006, 118, 776
22. Angew. Chem. Int. Ed. 2006, 45, 762
23. J. Simard-Mercier, A. B. Flynn, W. W. Ogilvie, Tetrahedron 2008, 64, 5472
24. N. Ishida, Y. Shimamoto, M. Murakami, Org. Lett. 2009, 11, 5434
25. K. Endo, M. Hirokami, T. Shibata, J. Org. Chem. 2010, 75, 3469
26. Y. Nishihara, Y. Okada, J. Jiao, M. Suetsugu, M.-T. Lan, M. Kinoshita, M. Iwasaki, K. Takagi, Angew. Chem. 2011, 123, 8819
27. Angew. Chem. Int. Ed. 2011, 50, 8660.
28. T. Vogler, A. Studer, Synthesis 2008, 1979
29. L. Tebben, A. Studer, Angew. Chem. 2011, 123, 5138
30. Angew. Chem. Int. Ed. 2011, 50, 5034.
31. S. Kirchberg, T. Vogler, A. Studer, Synlett 2008, 2841
32. M. S. Maji, T. Pfeifer, A. Studer, Angew. Chem. 2008, 120, 9690
33. Angew. Chem. Int. Ed. 2008, 47, 9547
34. J. Guin, S. De Sarkar, S. Grimme, A. Studer, Angew. Chem. 2008, 120, 8855
35. Angew. Chem. Int. Ed. 2008, 47, 8727
36. T. Vogler, A. Studer, Org. Lett. 2008, 10, 129
37. S. Kirchberg, R. Fröhlich, A. Studer, Angew. Chem. 2009, 121, 4299
38. Angew. Chem. Int. Ed. 2009, 48, 4235
39. S. Kirchberg, R. Fröhlich, A. Studer, Angew. Chem. 2010, 122, 7029
40. Angew. Chem. Int. Ed. 2010, 49, 6877
41. S. Kirchberg, S. Tani, K. Ueda, J. Yamaguchi, A. Studer, K. Itami, Angew. Chem. 2011, 123, 2435
42. Angew. Chem. Int. Ed. 2011, 50, 2387.
43. C. Wetter, J. Gierlich, C. A. Knoop, C. Müller, T. Schulte, A. Studer, Chem. Eur. J. 2004, 10, 1156
44. T. Schulte, K. O. Siegenthaler, H. Luftmann, M. Letzel, A. Studer, Macromolecules 2005, 38, 6833
45. C.-C. Chang, K. O. Siegenthaler, A. Studer, Helv. Chim. Acta 2006, 89, 2200
46. C.-C. Chang, A. Studer, Macromolecules 2006, 39, 4062.
47. S. Miele, P. Nesvadba, A. Studer, Macromolecules 2009, 42, 2419
48. I. C. Wienhöfer, A. Studer, Md. T. Rahman, T. Fukuyama, I. Ryu, Org. Lett. 2009, 11, 2457.
49. Reagent 8 can be readily prepared in analogy to TEMPO by replacing acetone with ethyl methyl ketone as a starting material, see:, H. Brunetti, J. Rody, N. Soma, T. Kurumada, DE-Patent, 2,621,841, 1976. 8 was used as a mixture of its 4 diastereoisomers: 65:14:13:8.
50. P. E. Tessier, A. J. Penwell, F. E. S. Souza, A. G. Fallis, Org. Lett. 2003, 5, 2989
51. N. F. McKinley, D. F. O'Shea, J. Org. Chem. 2006, 71, 9552
52. Y. Nishihara, M. Miyasaka, M. Okamoto, H. Takahashi, E. Inoue, K. Tanemura, K. Takagi, J. Am. Chem. Soc. 2007, 129, 12634.
53. J. A. Hadfield, A. T. McGown, J. Butler, Molecules 2000, 5, 82.