Room-temperature synthesis of trisubstituted allenylsilanes via regioselective c-h functionalization

Journal of the American Chemical Society

Volumn 135, Issue 49, 2013, Pages 18284-18287

  Zeng, Rong ^a   Wu, Shangze ^a   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT AIR; C-H FUNCTIONALIZATION; MECHANISTIC STUDIES; REGIO-SELECTIVE; ROOM TEMPERATURE SYNTHESIS; STRUCTURAL FEATURE;

FUNCTIONAL GROUPS;

REGIOSELECTIVITY;

BENZAMIDE DERIVATIVE; SILANE DERIVATIVE;

ALLYLATION; AMBIENT AIR; ARTICLE; CHEMICAL BOND; CYCLIZATION; ELECTRON; MOISTURE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOSPECIFICITY; SUZUKI REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 84890468813     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409861s     Document Type: Article

References (59)

1. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
2. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
3. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
4. Ackermann, L. Chem. Rev. 2011, 111, 1315
5. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
6. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
7. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
8. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
9. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
10. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
11. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170
12. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
13. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
14. Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592
15. Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
16. Ye, B.; Cramer, N. Science 2012, 338, 504
17. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
18. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
19. Wang, F.; Song, G.; Li, X. Org. Lett. 2010, 12, 5430
20. Willwacher, J.; Rakshit, S.; Glorius, F. Org. Biomol. Chem. 2011, 9, 4736
21. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
22. Li, X.; Gong, X.; Zhao, M.; Song, G.; Deng, J.; Li, X. Org. Lett. 2011, 13, 5808
23. Gong, T.-J.; Xiao, B.; Liu, Z.-J.; Wan, J.; Xu, J.; Luo, D.-F.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 3235
24. Besset, T.; Kuhl, N.; Patureau, F. W.; Glorius, F. Chem.-Eur. J. 2011, 17, 7167
25. Patureau, F. W.; Nimphius, C.; Glorius, F. Org. Lett. 2011, 13, 6346
26. Tsai, A. S.; Brasse, M.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2011, 13, 540
27. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
28. Park, S. H.; Kim, J. Y.; Chang, S. Org. Lett. 2011, 13, 2372
29. Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242
30. Zhen, W.; Wang, F.; Zhao, W.; Du, Z.; Li, X. Angew. Chem., Int. Ed. 2012, 51, 11819
31. Zhang, J.; Loh, T.-P. Chem. Commun. 2012, 48, 11232
32. Zheng, L.; Wang, J. Chem.-Eur. J. 2012, 18, 9699
33. Schröder, N.; Besset, T.; Glorius, F. Adv. Synth. Catal. 2012, 354, 579
34. Unoh, Y.; Hashimoto, Y.; Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258
35. Brasse, M.; Cámpora, J.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2013, 135, 6427
36. Liu, B.; Fan, Y.; Gao, Y.; Sun, C.; Xu, C.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 468
37. For a review on the regioselectivity of carbometallation of allenes, see: Bai, T.; Ma, S.; Jia, G. Coord. Chem. Rev. 2009, 253, 423
38. Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2010, 49, 8181
39. Tran, D. N.; Cramer, N. Chimia 2011, 65, 271
40. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
41. Zeng, R.; Ye, J.; Fu, C.; Ma, S. Adv. Synth. Catal. 2013, 355, 1963
42. Zeng, R.; Fu, C.; Ma, S. J. Am. Chem. Soc. 2012, 134, 9597
43. Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636
44. A theoretical study on conjugate addition vs Heck reaction: Peng, Q.; Yan, H.; Zhang, X.; Wu, Y. J. Org. Chem. 2012, 77, 7487
45. Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 125, 14342
46. Padala, K.; Jeganmohan, M. Org. Lett. 2011, 13, 6144
47. Karthikeyan, J.; Haridharan, R.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 12343
48. Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2012, 48, 2030
49. Padala, K.; Pimparkar, S.; Madasamy, P.; Jeganmohan, M. Chem. Commun. 2012, 48, 7140
50. Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565
51. Kornhaaß, C.; Li, J.; Ackermann, L. J. Org. Chem. 2012, 77, 9190
52. Parthasarathy, K.; Senthilkumar, N.; Jayakumar, J.; Cheng, C.-H. Org. Lett. 2012, 14, 3478
53. Padala, K.; Jeganmohan, M. Org. Lett. 2012, 14, 1134
54. Fleming, I. Org. React. 1989, 35, 501
55. Chai, G.; Zeng, R.; Fu, C.; Ma, S. Eur. J. Org. Chem. 2013, 148
56. Lü, B.; Fu, C.; Ma, S. Tetrahedron Lett. 2010, 51, 1284
57. Lü, B.; Fu, C.; Ma, S. Chem.-Eur. J. 2010, 16, 6434
58. Danheiser, R. L.; Tsai, Y.; Fink, D. M. Org. Synth. 1988, 66, 8
59. Brawn, R. A.; Panek, J. S. Org. Lett. 2010, 12, 4624