Cobalt-Catalyzed Bis-alkynylation of Amides via Double C-H Bond Activation

Organic Letters

Volumn 18, Issue 4, 2016, Pages 812-815

  Landge, Vinod G ^a,b   Jaiswal, Garima ^a,b   Balaraman, Ekambaram ^a,b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84958975356     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00095     Document Type: Article

References (88)

1. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624 10.1021/cr900005n
2. Ackermann, L. Chem. Commun. 2010, 46, 4866 10.1039/c0cc00778a
3. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 10.1021/cr900184e
4. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712 10.1039/B809912J
5. Ackermann, L. Chem. Rev. 2011, 111, 1315 10.1021/cr100412j
6. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740 10.1039/c1cs15083a
7. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879 10.1021/cr300153j
8. Collins, K. D.; Glorius, F. Nat. Chem. 2013, 5, 597 10.1038/nchem.1669
9. Zhang, X.-S.; Chen, K.; Shi, Z.-J. Chem. Sci. 2014, 5, 2146 10.1039/c3sc53115e
10. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087 10.1055/s-0029-1217131
11. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061 10.1021/jo100693m
12. Nakao, Y. Chem. Rec. 2011, 11, 242 10.1002/tcr.201100023
13. Yoshikai, N. Synlett 2011, 2011, 1047 10.1055/s-0030-1259928
14. Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 2013, 19 10.1002/ejoc.201200914
15. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726 10.1002/anie.201301451
16. Ackermann, L. J. Org. Chem. 2014, 79, 8948 10.1021/jo501361k
17. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299 10.1038/nature13274
18. Yoshikai, N. ChemCatChem 2015, 7, 732 10.1002/cctc.201403017
19. Diederich, F.; Stang, P. J.; Tykwinski, R. R. Acetylene Chemistry: Chemistry, Biology and Material Science; Wiley-VCH: Weinheim, 2005.
20. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46 10.1016/S0022-328X(02)01158-0
21. Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979 10.1021/cr020377i
22. Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742 10.1021/ja072718l
23. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250 10.1021/ol901049r
24. Gu, Y.; Wang, X. Tetrahedron Lett. 2009, 50, 763 10.1016/j.tetlet.2008.11.097
25. Kim, S. H.; Park, S. H.; Chang, S. Tetrahedron 2012, 68, 5162 10.1016/j.tet.2012.04.003
26. Ano, Y.; Tobisu, M.; Chatani, N. Synlett 2012, 23, 2763 10.1055/s-0032-1316556
27. Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2014, 53, 2722 10.1002/anie.201309198
28. Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780 10.1021/ja501910e
29. Shang, M.; Wang, H.-L.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 11590 10.1021/ja507704b
30. Liu, Y.-J.; Liu, Y.-H.; Yin, X.-S.; Gu, W.-J.; Shi, B.-F. Chem.-Eur. J. 2015, 21, 205 10.1002/chem.201405594
31. Liu, Y.-J.; Liu, Y.-H.; Yan, S.-Y.; Shi, B.-F. Chem. Commun. 2015, 51, 6388 10.1039/C5CC01163A
32. Liu, Y.-H.; Liu, Y.-J.; Yan, S.-Y.; Shi, B.-F. Chem. Commun. 2015, 51, 11650 10.1039/C5CC03729H
33. Yi, J.; Yang, L.; Xia, C.; Li, F. J. Org. Chem. 2015, 80, 6213 10.1021/acs.joc.5b00669
34. Landge, V. G.; Shewale, C. H.; Jaiswal, G.; Sahoo, M. K.; Midya, S. P.; Balaraman, E. Catal. Sci. Technol. 2016, 10.1039/C5CY01299F
35. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726 10.1002/anie.201301451
36. Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896 10.1002/anie.201303556
37. Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053 10.1021/ar5004626
38. Castro, L. C. M.; Chatani, N. Chem. Lett. 2015, 44, 410 10.1246/cl.150024
39. Rit, R. K.; Yadav, M. R.; Ghosh, K.; Sahoo, A. K. Tetrahedron 2015, 71, 4450 10.1016/j.tet.2015.03.085
40. Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2015, 6, 498 10.1021/acscatal.5b02344
41. Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 2207 10.1002/anie.201209226
42. Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Chem.-Eur. J. 2013, 19, 9142 10.1002/chem.201301505
43. Andou, T.; Saga, Y.; Komai, H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 3213 10.1002/anie.201208666
44. Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 1491 10.1002/adsc.201301110
45. Ikemoto, H.; Yoshino, T.; Sakata, K.; Matsunaga, S.; Kanai, M. J. Am. Chem. Soc. 2014, 136, 5424 10.1021/ja5008432
46. Yamamoto, S.; Saga, Y.; Andou, T.; Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 401 10.1002/adsc.201300991
47. Suzuki, Y.; Sun, B.; Sakata, K.; Yoshino, T.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2015, 54, 9944 10.1002/anie.201503704
48. Ilies, L.; Chen, Q.; Zeng, X.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 5221 10.1021/ja200645w
49. Chen, Q.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 428 10.1021/ja1099853
50. Chen, Q.; Ilies, L.; Yoshikai, N.; Nakamura, E. Org. Lett. 2011, 13, 3232 10.1021/ol2011264
51. Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53, 10209 10.1002/anie.201404579
52. Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4684 10.1021/ol502005g
53. Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4688 10.1021/ol502007t
54. Grigorjeva, L.; Daugulis, O. Org. Lett. 2015, 17, 1204 10.1021/acs.orglett.5b00155
55. Yu, D. G.; Gensch, T.; de Azambuja, F.; Vasquez-Cespedes, S.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17722 10.1021/ja511011m
56. Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508 10.1002/anie.201411994
57. Gensch, T.; Vasquez-Cespedes, S.; Yu, D.-G.; Glorius, F. Org. Lett. 2015, 17, 3714 10.1021/acs.orglett.5b01701
58. Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2010, 132, 12249 10.1021/ja106814p
59. Ding, Z.; Yoshikai, N. Org. Lett. 2010, 12, 4180 10.1021/ol101777x
60. Lee, P. S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 17283 10.1021/ja2047073
61. Gao, K.; Yoshikai, N. J. Am. Chem. Soc. 2013, 135, 9279 10.1021/ja403759x
62. Lee, P.-S.; Yoshikai, N. Org. Lett. 2015, 17, 22 10.1021/ol503119z
63. Yang, J.; Seto, Y. W.; Yoshikai, N. ACS Catal. 2015, 5, 3054 10.1021/acscatal.5b00581
64. Zhang, L. B.; Hao, X. Q.; Zhang, S. K.; Liu, Z. J.; Zheng, X. X.; Gong, J. F.; Niu, J. L.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 272 10.1002/anie.201409751
65. Zhang, L.-B.; Hao, X.-Q.; Liu, Z.-J.; Zheng, X.-X.; Zhang, S.-K.; Niu, J.-L.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 10012 10.1002/anie.201504962
66. Song, W.; Ackermann, L. Angew. Chem., Int. Ed. 2012, 51, 8251 10.1002/anie.201202466
67. Punji, B.; Song, W.; Shevchenko, G. A.; Ackermann, L. Chem.-Eur. J. 2013, 19, 10605 10.1002/chem.201301409
68. Li, J.; Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 8551 10.1002/anie.201501926
69. Moselage, M.; Sauermann, N.; Koeller, J.; Liu, W.; Gelman, D.; Ackermann, L. Synlett 2015, 26, 1596 10.1055/s-0034-1379927
70. Ma, W.; Ackermann, L. ACS Catal. 2015, 5, 2822 10.1021/acscatal.5b00322
71. Li, J.; Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 3635 10.1002/anie.201409247
72. Sauermann, N.; Gonzalez, M. J.; Ackermann, L. Org. Lett. 2015, 17, 5316 10.1021/acs.orglett.5b02678
73. Ma, W.; Ackermann, L. ACS Catal. 2015, 5, 2822 10.1021/acscatal.5b00322
74. Li, J.; Ackermann, L. Chem.-Eur. J. 2015, 21, 5718 10.1002/chem.201500552
75. Moselage, M.; Sauermann, N.; Richter, S. C.; Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 6352 10.1002/anie.201412319
76. Pawar, A. B.; Chang, S. Org. Lett. 2015, 17, 660 10.1021/ol503680d
77. Patel, P.; Chang, S. ACS Catal. 2015, 5, 853 10.1021/cs501860b
78. Hummel, J. R.; Ellman, J. A. J. Am. Chem. Soc. 2015, 137, 490 10.1021/ja5116452
79. Hummel, J. R.; Ellman, J. A. Org. Lett. 2015, 17, 2400 10.1021/acs.orglett.5b00910
80. Sen, M.; Kalsi, D.; Sundararaju, B. Chem.-Eur. J. 2015, 21, 15529 10.1002/chem.201503643
81. Zhang, J.; Chen, H.; Lin, C.; Liu, Z.; Wang, C.; Zhang, Y. J. Am. Chem. Soc. 2015, 137, 12990 10.1021/jacs.5b07424
82. Zhang, Z.-Z.; Liu, B.; Wang, C.-Y.; Shi, B.-F. Org. Lett. 2015, 17, 4094 10.1021/acs.orglett.5b02038
83. 2OH, proved ineffective in the C-H bond alkynylation.
84. 3 proved ineffective, and less formation (up to ∼30%) of 3a was observed under optimal conditions.
85. 3 did not improve the yield of the alkynylated product 3a under optimal conditions (see the Table 1, entries 8-9).
86. Compound 3e′ (yield = 45%) was prepared under condition B.
87. Fang, G.; Bi, X. Chem. Soc. Rev. 2015, 44, 8124 10.1039/C5CS00027K
88. Wu, X.; Yang, K.; Zhao, Y.; Sun, H.; Li, G.; Ge, H. Nat. Commun. 2015, 6, 6462 10.1038/ncomms7462