Rh(III)-catalyzed dehydrogenative alkylation of (hetero)arenes with allylic alcohols, allowing aldol condensation to indenes

Chemical Communications

Volumn 49, Issue 58, 2013, Pages 6489-6491

  Shi, Zhuangzhi ^a   Boultadakis Arapinis, Mélissa ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; ALLYLIC ALCOHOL; HETEROCYCLIC COMPOUND; INDENE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ARTICLE; CATALYSIS; DEHYDROGENATION;

EID: 84879764609     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc43903h     Document Type: Article

References (57)

1. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res., 2012, 45, 788.
2. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res., 2012, 45, 936.
3. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed., 2012, 51, 8960.
4. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev., 2012, 41, 5588.
5. J. Wencel-Delord, F. Glorius, Nat. Chem., 2013, 5, 369.
6. T. Satoh, M. Miura, Chem. Eur. J., 2010, 16, 11212.
7. G. Song, F. Wang, X. Li, Chem. Soc. Rev., 2012, 41, 3651.
8. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta, 2012, 45, 31.
9. T. L. Hyster, L. Knörr, T. R. Ward, T. Rovis, Science, 2012, 338, 500.
10. B. Ye, N. Cramer, Science, 2012, 338, 504.
11. Z. Shi, N. Schröder, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 8092.
12. J. Jayakumar, K. Parthasarathy, C.-H. Cheng, Angew. Chem., Int. Ed., 2012, 51, 197.
13. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem., Int. Ed., 2012, 51, 3948.
14. W. Zhen, F. Wang, M. Zhao, Z. Du, X. Li, Angew. Chem., Int. Ed., 2012, 51, 11819.
15. D. Wang, F. Wang, G. Song, X. Li, Angew. Chem., Int. Ed., 2012, 51, 12348.
16. R. Zeng, C. Fu, S. Ma, J. Am. Chem. Soc., 2012, 134, 9597.
17. H. Wang, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 7318.
18. X. Tan, B. Liu, X. Li, B. Li, S. Xu, H. Song, B. Wang, J. Am. Chem. Soc., 2012, 134, 16163.
19. N. Kuhl, M. N. Hopkinson, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 8230.
20. N. Schröder, J. Wencel-Delord, F. Glorius, J. Am. Chem. Soc., 2012, 134, 8298.
21. J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 2247.
22. J. Wencel-Delord, C. Nimphius, H. Wang, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 13001.
23. H. Wang, C. Grohmann, C. Nimphius, F. Glorius, J. Am. Chem. Soc., 2012, 134, 19592.
24. B. Ye, N. Cramer, J. Am. Chem. Soc., 2013, 135, 636.
25. Y. Lian, T. Huber, K. D. Hesp, R. G. Bergman, J. A. Ellman, Angew. Chem., Int. Ed., 2013, 52, 629.
26. J. M. Neely, T. Rovis, J. Am. Chem. Soc., 2013, 135, 66.
27. J. Dong, Z. Long, F. Song, N. Wu, Q. Guo, J. Lan, J. You, Angew. Chem., Int. Ed., 2013, 52, 580.
28. H. Wang, N. Schröder, F. Glorius, Angew. Chem., Int. Ed., 2013, 52, 5386.
29. Z. Shi, C. Grohmann, F. Glorius, Angew. Chem., Int. Ed., 2013, 52, 5393.
30. T. K. Hyster, K. E. Ruhl, T. Rovis, J. Am. Chem. Soc., 2013, 135, 5364.
31. R. F. Heck, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, New York, 1991, ch. 4.3, vol. 4
32. S. Bräse, and A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions, ed. A. de Meijere and F. Diederich, Wiley-VCH, New York, 2004, ch. 5
33. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev., 2000, 100, 3009.
34. A. B. Dounay, L. E. Overman, Chem. Rev., 2003, 103, 2945.
35. J. Muzart, Tetrahedron, 2005, 61, 4179.
36. K. Matoba, S.-I. Motofusa, C. S. Cho, K. Ohe, S. Uemura, J. Organomet. Chem., 1999, 574, 3.
37. M. Chen, J. Wang, Z. Chai, C. You, A. Lei, Adv. Synth. Catal., 2012, 354, 341.
38. E. W. Werner, T.-S. Mei, A. J. Burckle, M. S. Sigman, Science, 2012, 338, 1455.
39. C. C. Oliveira, R. A. Angnes, C. R. D. Correia, J. Org. Chem., 2013, 78, 4373.
40. R. J. Sundberg, Indoles, Academic Press, San Diego, 1996
41. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
42. M. Somei, F. Yamada, Nat. Prod. Rep., 2005, 22, 73.
43. L. Jiao, T. Bach, J. Am. Chem. Soc., 2011, 133, 12990.
44. L. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc., 2012, 134, 14563.
45. A. García-Rubia, B. Urones, R. G. Arrayás, J. C. Carreter, Chem. Eur. J., 2010, 16, 9676.
46. F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc., 2011, 133, 2154.
47. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem., Int. Ed., 2011, 50, 4169.
48. Y. Kuninobu, Y. Nishina, M. Shouho, K. Takai, Angew. Chem., Int. Ed., 2006, 45, 2766.
49. X.-Y. Shi, C.-J. Li, Org. Lett., 2013, 15, 1476.
50. L. Yang, B. Qian, H. Huang, Chem. Eur. J., 2012, 18, 9511.
51. T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kana, Angew. Chem., Int. Ed., 2013, 52, 2207.
52. J. A. R. Salvador, S. M. Silvestre, V. M. Moreira, Curr. Org. Chem., 2006, 10, 2227.
53. T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J., 2008, 3, 196.
54. S. B. Han, I. S. Kim, M. J. Krische, Chem. Commun., 2009, 7278.
55. Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev., 2012, 41, 3381.
56. K. Fujita, Y. Takahashi, M. Owaki, K. Yamamoto, R. Yamaguchi, Org. Lett., 2004, 6, 2785.
57. L. Huang, Q. Wang, J. Qi, X. Wu, K. Huang, H. Jiang, Chem. Sci., 2013, 4, 2665.