Arene C-H Bond Functionalization Coupling with Cyclization of Allenes

Advanced Synthesis and Catalysis

Volumn 355, Issue 10, 2013, Pages 1963-1970

  Zeng, Rong ^a   Ye, Juntao ^b   Fu, Chunling ^a   Ma, Shengming ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2,3 allenols; 2,5 dihydrofurans; C H activation; coupling cyclization; rhodium catalysts

Indexed keywords

EID: 84880812846     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300408     Document Type: Article

References (64)

1. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
2. J. L. Bras, J. Muzart, Chem. Rev. 2011, 111, 1170
3. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
4. L. Ackermann, Chem. Rev. 2011, 111, 1315
5. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
6. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293
7. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
8. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
9. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885
10. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382
11. Angew. Chem. Int. Ed. 2012, 51, 10236.
12. I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858
13. L. Zhang, J. Cheng, T. Ohishi, Z. Hou, Angew. Chem. 2010, 122, 8852
14. Angew. Chem. Int. Ed. 2010, 49, 8670
15. H. Mizuno, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2011, 133, 1251.
16. Y. J. Zhang, E. Skucas, M. J. Krische, Org. Lett. 2009, 11, 4248
17. D. N. Tran, N. Cramer, Angew. Chem. 2010, 122, 8357
18. Angew. Chem. Int. Ed. 2010, 49, 8181
19. D. N. Tran, N. Cramer, Chimia 2011, 65, 271
20. Y. Kuninobu, P. Yu, K. Takai, Org. Lett. 2010, ##12, 4274
21. R. Zeng, C. Fu, S. Ma, J. Am. Chem. Soc. 2012, 134, 9597
22. B. Ye, N. Cramer, J. Am. Chem. Soc. 2013, 135, 636
23. H. Wang, F. Glorius, Angew. Chem. 2012, 124, 7430
24. Angew. Chem. Int. Ed. 2012, 51, 7318.
25. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12
26. S. Ma, Acc. Chem. Res. 2003, 36, 701
27. S. Ma, in: Topics in Organometallic Chemistry, (Ed.:, J. Tsuji,), Springer-Verlag, Heidelberg, 2005, pp 183-210.
28. Modern Allene Chemistry, (Eds.:, N. Krause, A. S. K. Hashmi,), Wiley-VCH, Weinheim, 2004
29. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067
30. A. Hoffmann-Röder, N. Krause, Angew. Chem. 2002, 114, 3057
31. Angew. Chem. Int. Ed. 2002, 41, 2933
32. L. K. Sydnes, Chem. Rev. 2003, 103, 1133
33. S. Ma, Chem. Rev. 2005, 105, 2829
34. S. Ma, Aldrichimica Acta 2007, 40, 91
35. B. Alcaide, P. Almendros, T. M. del Campo, Chem. Eur. J. 2010, 16, 5836.
36. Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381
37. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329
38. K. M. Gligorich, M. S. Sigman, Chem. Commun. 2009, 3854
39. S. S. Stahl, Angew. Chem. 2004, 116, 3480
40. Angew. Chem. Int. Ed. 2004, 43, 3400
41. A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851
42. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740.
43. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
44. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
45. T. K. Hyster, T. Rovis, Chem. Sci. 2011, 2, 1606
46. N. Schröder, T. Besset, F. Glorius, Adv. Synth. Catal. 2012, 354, 579
47. L. Zheng, J. Wang, Chem. Eur. J. 2012, 18, 9699.
48. F. M. Dean, M. V. Sargent, in: Comprehensive Heterocyclic Chemistry, (Eds.:, A. R. Karitzky, C. W. Rees,), Pergamon, Oxford, 1984, Vol. 4, pp 531- 712
49. R. Benassi, in: Comprehensive Heterocyclic Chemistry II. (Eds.:, A. R. Karitzky, C. W. Rees, E. F. V. Scriven,), Pergamon, Oxford, 1996, Vol. 2, pp 259- 436.
50. int=0.0406), number of observations [>2σ(I)] 4613, parameters: 565. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre under CCDC 929374. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. T. Satoh, Y. Nishinaka, M. Miura, M. Nomura, Chem. Lett. 1999, 615
52. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820
53. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740.
54. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908
55. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350.
56. J. Ye, S. Li, B. Chen, W. Fan, J. Kuang, J. Liu, Y. Liu, B. Miao, B. Wan, Y. Wang, X. Xie, Q. Yu, W. Yuan, S. Ma, Org. Lett. 2012, 14, 1346
57. J. Ye, W. Fan, S. Ma, Chem. Eur. J. 2013, 19, 716.
58. For a review on different insertion reactions of allenes with metallic species, see:, T. Bai, S. Ma, G. Jia, Coord. Chem. Rev. 2009, 253, 423.
59. A. Lumbroso, P. Koschker, N. R. Vautravers, B. Breit, J. Am. Chem. Soc. 2011, 133, 2386
60. P. Koschker, A. Lumbroso, B. Breit, J. Am. Chem. Soc. 2011, 133, 20746
61. M. L. Cooke, K. Xu, B. Breit, Angew. Chem. 2012, 124, 11034
62. Angew. Chem. Int. Ed. 2012, 51, 10876.
63. For a selected report on Rh-catalyzed enantioselective allylic alkylation of propenyl acetate via π-allyl rhodium intermediates, see:, T. Hayashi, A. Okasa, T. Suzuka, M. Kawatsura, Org. Lett. 2003, 5, 1713.
64. For a report on Rh-catalyzed allylic alkylation of 1,3-disubstituted allylic carbonate with partial racemization from 98% ee to 90% ee, see:, P. A. Evans, J. D. Nelson, J. Am. Chem. Soc. 1998, 120, 5581.