Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1544-1547

  Liao, Yuan Xi ^a   Xing, Chun Hui ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BORONIC ACID DERIVATIVE; KETONE; RHODIUM;

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

ALCOHOLS; BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; RHODIUM;

EID: 84858692524     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300275s     Document Type: Article

References (66)

1. Partyka, D. V. Chem. Rev. 2011, 111, 1529-1595
2. Miyaura, N. Synlett 2009, 2039-2050
3. Gutnov, A. Eur. J. Org. Chem. 2008, 4547-4554
4. Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364-3366
5. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844
6. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196 and references cited therein
7. Morikawa, S.; Michigami, K.; Amii, H. Org. Lett. 2010, 12, 2520-2523
8. Trindade, A. F.; Andre, V.; Duarte, M. T.; Veiros, L. F.; Gois, P. M. P.; Afonso, C. A. M. Tetrahedron 2010, 66, 8494-8502
9. Ma, Q.; Ma, Y.; Liu, X.; Duan, W.; Qu, B.; Song, C. Tetrahedron: Asymmetry 2010, 21, 292-298
10. White, J. R.; Price, G. J.; Plucinski, P. K.; Frost, C. G. Tetrahedron Lett. 2009, 50, 7365-7368
11. Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876-1877
12. Trenkle, W. C.; Barkin, J. L.; Son, S. U.; Sweigart, D. A. Organometallics 2006, 25, 3548-3551
13. Yamamoto, T.; Iizuka, M.; Takenaka, H.; Ohta, T.; Ito., Y. J. Organomet. Chem. 2009, 694, 1325-1332
14. Lu, X.; Lin, S. J. Org. Chem. 2005, 70, 9651-9653
15. Bedford, R. B.; Betham, M.; Charmant, J. P. H; Haddow, M. F. A.; Orpen, G.; Pilarski, L. T.; Coles, S. J.; Hursthouse, M. B. Organometallics 2007, 26, 6346-6353
16. Nishikata, T.; Yamamoto, Y.; Miyaura, N. Organometallics 2004, 23, 4317-4324
17. Bouffard, J.; Itami, K. Org. Lett. 2009, 11, 4410-4413
18. Zhou, L.; Du, X.; He, R.; Ci, Z.; Bao, M. Tetrahedron Lett. 2009, 50, 406-408
19. Sakurai, F.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2009, 50, 6001-6003
20. Yamamoto, K.; Tsurumi, K.; Sakurai, F.; Kondo, K.; Aoyama, T. Synthesis 2008, 3585-3590
21. Arao, T.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2007, 48, 4115-4117
22. Takahashi, G.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2005, 1459-1461
23. Maekawa, T.; Sekizawa, H.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 7022-7026
24. Tomita, D.; Kanai, M.; Shibasaki, M. Chem. - Asian J. 2006, 1, 161-166
25. Zheng, H.; Zhang, Q.; Chen, J.; Liu, M.; Cheng, S.; Ding, J.; Wu, H.; Su, W. J. Org. Chem. 2009, 74, 943-945
26. Zou, T.; Pi, S.-S.; Li, J.-H. Org. Lett. 2009, 11, 453-456
27. Yamamoto, Y.; Kurihara, K.; Miyaura, N. Angew. Chem., Int. Ed. 2009, 48, 4414-4416
28. Karthikeyan, J.; Jeganmohan, M.; Cheng, C.-H. Chem. - Eur. J. 2010, 16, 8989-8992
29. He, P.; Lu, Y.; Dong, C.-G.; Hu, Q.-S. Org. Lett. 2007, 9, 343-346
30. He, P.; Lu, Y.; Hu, Q.-S. Tetrahedron Lett. 2007, 48, 5283-5288
31. Duan, H.-F.; Xie, J.-H.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2008, 47, 4351-4353
32. Cai, F.; Pu, X.; Qi, X.; Lynch, V.; Radha, A.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 18066-18069
33. Ganci, G. R.; Chisholm, J. D. Tetrahedron Lett. 2007, 48, 8266-8269
34. Miyamura, S.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 2255-2257
35. Shintani, R.; Takatsu, K.; Hayashi, T. Chem. Commun. 2010, 46, 6822-6824
36. Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353-3356
37. Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715-2718
38. Liu, Z.; Gu, P.; Shi, M.; McDowell, P.; Li, G. Org. Lett. 2011, 13, 2314-2317
39. Lai, H.; Huang, Z.; Wu, Q.; Qin, Y. J. Org. Chem. 2009, 74, 283-288
40. Jumde, V. R.; Facchetti, S.; Iuliano, A. Tetrahedron: Asymmetry 2010, 21, 2775-2781
41. Martina, S. L. X.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2006, 4093-4095
42. Liu, G.; Lu, X. J. Am. Chem. Soc. 2006, 128, 16504-16505
43. Liu, G.; Lu, X. Tetrahedron 2008, 64, 7324-7330
44. Iuliano, A.; Facchetti, S.; Funaioli, T. Chem. Commun. 2009, 46, 6822-6824
45. Facchetti, S.; Cavallini, I.; Funaioli, T.; Marchetti, F.; Iuliano, A. Organometallics 2009, 28, 4150-4158
46. Iuliano, A.; Facchetti, S.; Funaioli, T. Chem. Commun. 2009, 457-459
47. Vandyck, K.; Matthys, B.; Willen, M.; Robeyns, K.; Van Meervelt, L.; Van der Eycken, J. Org. Lett. 2006, 8, 363-366
48. Ueura, K.; Miyamura, S.; Satoh, T.; Miura, M. J. Organomet. Chem. 2006, 691, 2821-2826
49. Korenaga, T.; Hayashi, K.; Akaki, Y.; Maenishi, R.; Sakai, T. Org. Lett. 2011, 13, 2022-2025
50. 2/electron-poor bisphosphine BFPY-catalyzed addition reactions of arylboronic acids with unactivated ketones, with one example of asymmetric addition in 38% ee: Korenaga, T.; Ko, A.; Uotani, K.; Tanaka, Y.; Sakai, T. Angew. Chem., Int. Ed. 2011, 50, 10703-10706
51. Liao, Y.-X.; Xing, C.-H.; Israel, M.; Hu, Q.-S. Tetrahedron Lett. 2011, 52, 3324-3328
52. Liao, Y.-X.; Xing, C.-H.; He, P.; Hu, Q.-S. Org. Lett. 2008, 10, 2509-2512
53. Xing, C.-H.; Liu, T.-P.; Zheng, J. R.; Ng, J.; Esposito, M.; Hu, Q.-S. Tetrahedron Lett. 2009, 50, 4953-4957
54. Xing, C.-H.; Liao, Y.-X.; He, P.; Hu, Q.-S. Chem. Commun. 2010, 3010-3012
55. Liao, Y.-X.; Hu, Q.-S. J. Org. Chem. 2011, 76, 7602-7607
56. Xing, C.-H.; Hu, Q.-S. Tetrahedron Lett. 2010, 51, 924-927
57. Liu, T.-P.; Liao, Y.-X.; Xing, C.-H.; Hu, Q.-S. Org. Lett. 2011, 13, 2452-2455
58. Liao, Y.-X.; Xing, C.-H.; Israel, M.; Hu, Q.-S. Org. Lett. 2011, 13, 2058-2061
59. Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. Synlett 2011, 1345-1356
60. Shintani, R.; Hayashi, T. Aldrichimica Acta 2009, 42, 31-38
61. Defieber, C.; Grutzmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482-4502
62. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840-871
63. Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364-3366
64. Wang, Z.-Q.; Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. J. Am. Chem. Soc. 2007, 129, 5336-5337
65. Wang, Z.-Q.; Feng, C.-G.; Zhang, S.-S.; Xu, M.-H.; Lin, G.-Q. Angew. Chem., Int. Ed. 2010, 49, 5780-5783
66. For an example of Rh(I)-catalyzed addition reactions of arylboronic acids with aldehydes with KF as the base: Duan, H.-F.; Xie, J.-H.; Shi, W.-J.; Zhang, Q.; Zhou, Q.-L. Org. Lett. 2006, 8, 1479-1481