Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: A practical entry to 2,2-disubstituted 2H-chromenes

Angewandte Chemie - International Edition

Volumn 54, Issue 8, 2015, Pages 2374-2377

  Casanova, Noelia ^a   Seoane, Andrés ^a   Mascareñas, José L ^a   Gulías, Moisés ^a  

^a s n   (Spain)

Author keywords

Allenes; Annulations; C H activation; Reaction mechanisms; Rhodium

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; RHODIUM;

ALLENES; ANNULATIONS; C-H ACTIVATION; HETEROANNULATION; REACTION MECHANISM; RHODIUM CATALYSIS; RHODIUM-CATALYZED; WHOLE PROCESS;

HYDROCARBONS;

EID: 85027930477     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410350     Document Type: Article

References (56)

1. a) C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215;
2. b) G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651;
3. c) J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369;
4. d) K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788;
5. e) T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212;
6. f) L. Ackermann, Acc. Chem. Res. 2014, 47, 281.
7. a) J. M. Neely, T. Rovis, J. Am. Chem. Soc. 2013, 135, 66;
8. b) N. Quiñones, A. Seoane, R. Garcia-Fandiño, J. L. Mascareñas, M. Gulías, Chem. Sci. 2013, 4, 2874;
9. c) C.-Z. Luo, P. Gandeepan, C.-H. Cheng, Chem. Commun. 2013, 49, 8528;
10. d) J. R. Huckins, E. A. Bercot, O. R. Thiel, T.-L. Hwang, M. M. Bio, J. Am. Chem. Soc. 2013, 135, 14492;
11. e) J. D. Dooley, S. Reddy Chidipudi, H. W. Lam, J. Am. Chem. Soc. 2013, 135, 10829;
12. f) D. Zhao, Z. Shi, F. Glorius, Angew. Chem. Int. Ed. 2013, 52, 12426;
13. Angew. Chem. 2013, 125, 12652;
14. g) J. Nan, Z. Zuo, L. Luo, L. Bai, H. Zheng, Y. Yuan, J. Liu, X. Luan, Y. Wang, J. Am. Chem. Soc. 2013, 135, 17306;
15. h) M. V. Pham, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 3484;
16. Angew. Chem. 2014, 126, 3552;
17. i) D. J. Burns, H. W. Lam, Angew. Chem. Int. Ed. 2014, 53, 9931;
18. Angew. Chem. 2014, 126, 10089;
19. j) D.-G. Yu, F. de Azambuja, T. Gensch, C. G. Daniliuc, F. Glorius, Angew. Chem. Int. Ed. 2014, 53, 9650;
20. Angew. Chem. 2014, 126, 9804;
21. k) T. Piou, T. Rovis, J. Am. Chem. Soc. 2014, 136, 11292.
22. a) A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 834;
23. b) A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 7607;
24. c) S. Kujawa, D. Best, D. J. Burns, H. W. Lam, Chem. Eur. J. 2014, 20, 8599.
25. a) H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 7318;
26. Angew. Chem. 2012, 124, 7430;
27. b) R. R. Suresh, K. C. K. Swamy, J. Org. Chem. 2012, 77, 6959;
28. c) X.-F. Xia, Y.-Q. Wang, L.-L. Zhang, X.-R. Song, X.-Y. Liu, Y.-M. Liang, Chem. Eur. J. 2014, 20, 5087;
29. d) A. Rodríguez, J. Albert, X. Ariza, J. Garcia, J. Granell, J. Farràs, A. La Mela, E. Nicolás, J. Org. Chem. 2014, 79, 9578.
30. a) H. Wang, B. Beiring, D.-G. Yu, K. D. Collins, F. Glorius, Angew. Chem. Int. Ed. 2013, 52, 12430;
31. Angew. Chem. 2013, 125, 12657;
32. b) R. Zeng, C. Fu, S. Ma, J. Am. Chem. Soc. 2012, 134, 9597;
33. c) R. Zeng, S. Wu, C. Fu, S. Ma, J. Am. Chem. Soc. 2013, 135, 18284;
34. d) T.-J. Gong, W. Su, Z.-J. Liu, W.-M. Cheng, B. Xiao, Y. Fu, Org. Lett. 2014, 16, 330;
35. e) R. Zeng, J. Ye, C. Fu, S. Ma, Adv. Synth. Catal. 2013, 355, 1963;
36. f) B. Ye, N. Cramer, J. Am. Chem. Soc. 2013, 135, 636;
37. g) D. N. Tran, N. Cramer, Angew. Chem. Int. Ed. 2010, 49, 8181;
38. Angew. Chem. 2010, 122, 8357;
39. h) D. N. Tran, N. Cramer, Angew. Chem. Int. Ed. 2013, 52, 10630;
40. Angew. Chem. 2013, 125, 10824.
41. a) P. N. Moquist, T. Kodama, S. E. Schaus, Angew. Chem. Int. Ed. 2010, 49, 7096;
42. Angew. Chem. 2010, 122, 7250;
43. b) N. Majumdar, K. A. Korthals, W. D. Wulff, J. Am. Chem. Soc. 2012, 134, 1357;
44. c) T. J. A. Graham, A. G. Doyle, Org. Lett. 2012, 14, 1616;
45. d) A. J. Walkinshaw, W. Xu, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 12532;
46. e) N. D. Paul, S. Mandal, M. Otte, X. Cui, X. P. Zhang, B. de Bruin, J. Am. Chem. Soc. 2014, 136, 1090;
47. f) S. E. Ammann, G. T. Rice, M. C. White, J. Am. Chem. Soc. 2014, 136, 10834;
48. g) U. Uria, C. Vila, M.-Y. Lin, M. Rueping, Chem. Eur. J. 2014, 20, 13913.
49. Styrene and cyclohexene were the alkenes tested.
50. Concerted metalation-deprotonation (CMD) mechanisms, generally proposed for the C-H activation step with palladium(II), ruthenium(II), or rhodium(III), should provide nondeuterated products.
51. The presence of a phenyl substituent in the intermediate 6 increases its thermal stability. In most of the other reactions, the dienic intermediates are not detected at 85°C, whereas at room temperature they evolve to the chromene products in minutes.
52. The isolation of the intermediate 6 serves to eliminate the alternative mechanism involving the formation of a rhodacyclobutane by intramolecular nucleophilic attack of the phenoxide to the central carbon of the π-allyl rhodium (C), followed by β-hydride elimination and reductive elimination.
53. An intermediate with an acetate or chloride still bound to rhodium could be also proposed: (Chemical Equation Presented).
54. This may involve a previous protonolysis step of the Rh-O bond by AcOH.
55. a) D. B. Ramachary, V. V. Narayana, K. Ramakumar, Eur. J. Org. Chem. 2008, 3907;
56. b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875.