Cp∗CoIII-Catalyzed Dehydrative C-H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols

Organic Letters

Volumn 18, Issue 9, 2016, Pages 2216-2219

  Bunno, Youka ^a   Murakami, Nanami ^a   Suzuki, Yudai ^b   Kanai, Motomu ^b   Yoshino, Tatsuhiko ^a,c   Matsunaga, Shigeki ^a,c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84969695734     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00846     Document Type: Article

References (95)

1. Trost, B. M. Science 1991, 254, 1471 10.1126/science.1962206
2. Wender, P. A.; Miller, B. L. Nature 2009, 460, 197 10.1038/460197a
3. Ackermann, L. Org. Process Res. Dev. 2015, 19, 260 10.1021/op500330g
4. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726 10.1002/anie.201301451
5. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369 10.1038/nchem.1607
6. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960 10.1002/anie.201201666
7. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936 10.1021/ar300014f
8. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788 10.1021/ar200185g
9. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068 10.1039/c1cs15082k
10. Magid, R. M. Tetrahedron 1980, 36, 1901 10.1016/0040-4020(80)80203-1
11. Pigge, F. C. Synthesis 2010, 2010, 1745 10.1055/s-0029-1218756
12. Farmer, J. L.; Hunter, H. N.; Organ, M. G. J. Am. Chem. Soc. 2012, 134, 17470 10.1021/ja308613b
13. Yang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 10642 and references therein 10.1021/ja405950c
14. Although direct allylation of aromatic C-H bonds is possible via Friedel-Crafts allylation, low regioselectivity, over-allylation, and limited substrate scope are often problematic: Rueping, M.; Nachtsheim, B. J. Beilstein J. Org. Chem. 2010, 6, doi: 10.3762/bjoc.6.6.
15. Oi, S.; Tanaka, Y.; Inoue, Y. Organometallics 2006, 25, 4773 10.1021/om060561k
16. Kuninobu, Y.; Ohta, K.; Takai, K. Chem. Commun. 2011, 47, 10791 10.1039/c1cc12359a
17. Feng, C.; Feng, D.; Loh, T.-P. Chem. Commun. 2015, 51, 342 10.1039/C4CC07597H
18. Fan, S.; Chen, F.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 5918 10.1002/anie.201008174
19. Wang, H.; Schröder, N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386 10.1002/anie.201301165
20. Zhang, S.-S.; Wu, J.-Q.; Lao, Y.-X.; Liu, X.-G.; Liu, Y.; Lv, W.-X.; Tan, D.-H.; Zeng, Y.-F.; Wang, H. Org. Lett. 2014, 16, 6412 10.1021/ol503229c
21. Sharma, S.; Shin, Y.; Mishra, N. K.; Park, J.; Han, S.; Jeong, T.; Oh, Y.; Lee, Y.; Choi, M.; Kim, I. S. Tetrahedron 2015, 71, 2435 10.1016/j.tet.2015.02.052
22. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2011, 50, 2990 10.1002/anie.201007733
23. Makida, Y.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2012, 51, 4122 10.1002/anie.201200809
24. Cong, X.; Li, Y.; Wei, Y.; Zeng, X. Org. Lett. 2014, 16, 3926 10.1021/ol501707z
25. Jo, H.; Han, S.; Park, J.; Choi, M.; Han, S. H.; Jeong, T.; Lee, S.-Y.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Tetrahedron 2016, 72, 571 10.1016/j.tet.2015.12.029
26. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308 10.1021/ja401344e
27. Yu, Y.-B.; Fan, S.; Zhang, X. Chem.-Eur. J. 2012, 18, 14643 10.1002/chem.201202824
28. Xie, W.; Chang, S. Angew. Chem., Int. Ed. 2016, 55, 1876 10.1002/anie.201510180
29. Dai, H.; Yu, C.; Lu, C.; Yan, H. Eur. J. Org. Chem. 2016, 2016, 1255 10.1002/ejoc.201501551
30. Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 17755 10.1021/ja4106368
31. Yu, S.; Li, X. Org. Lett. 2014, 16, 1200 10.1021/ol5000764
32. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212 10.1002/chem.201001363
33. Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31
34. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651 10.1039/c2cs15281a
35. Chiba, S. Chem. Lett. 2012, 41, 1554 10.1246/cl.2012.1554
36. Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443 10.1002/adsc.201400197
37. Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007 10.1021/acs.accounts.5b00077
38. Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308 10.1021/acs.accounts.5b00092
39. Zeng, R.; Fu, C.; Ma, S. J. Am. Chem. Soc. 2012, 134, 9597 10.1021/ja303790s
40. Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636 10.1021/ja311956k
41. Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 2207 10.1002/anie.201209226
42. Ikemoto, H.; Yoshino, T.; Sakata, K.; Matsunaga, S.; Kanai, M. J. Am. Chem. Soc. 2014, 136, 5424 10.1021/ja5008432
43. Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 1491 10.1002/adsc.201301110
44. Sun, B.; Yoshino, T.; Kanai, M.; Matsunaga, S. Angew. Chem., Int. Ed. 2015, 54, 12968 10.1002/anie.201507744
45. Recent review: Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2016, 6, 498 10.1021/acscatal.5b02344
46. Hummel, J. R.; Ellman, J. A. J. Am. Chem. Soc. 2015, 137, 490 10.1021/ja5116452
47. Patel, P.; Chang, S. ACS Catal. 2015, 5, 853 10.1021/cs501860b
48. Li, J.; Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 3635 10.1002/anie.201409247
49. Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508 10.1002/anie.201411994
50. Zhang, Z.-Z.; Liu, B.; Wang, C.-Y.; Shi, B.-F. Org. Lett. 2015, 17, 4094 10.1021/acs.orglett.5b02038
51. Sauermann, N.; González, M. J.; Ackermann, L. Org. Lett. 2015, 17, 5316 10.1021/acs.orglett.5b02678
52. Park, J.; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 14103 10.1002/anie.201505820
53. Sen, M.; Kalsi, D.; Sundararaju, B. Chem.-Eur. J. 2015, 21, 15529 10.1002/chem.201503643
54. Barsu, N.; Sen, M.; Premkumar, J. R.; Sundararaju, B. Chem. Commun. 2016, 52, 1338 10.1039/C5CC08736H
55. Prakash, S.; Muralirajan, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2016, 55, 1844 10.1002/anie.201509316
56. Lerchen, A.; Vásquez-Céspedes, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 3208 10.1002/anie.201510705
57. Liang, Y.; Jiao, N. Angew. Chem., Int. Ed. 2016, 55, 4035 10.1002/anie.201511002
58. Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53, 10209 10.1002/anie.201404579
59. Wu, X.; Yang, K.; Zhao, Y.; Sun, H.; Li, G.; Ge, H. Nat. Commun. 2015, 6, 6462 10.1038/ncomms7462
60. Zhang, J.; Chen, H.; Lin, C.; Liu, Z.; Wang, C.; Zhang, Y. J. Am. Chem. Soc. 2015, 137, 12990 10.1021/jacs.5b07424
61. Kalsi, D.; Sundararaju, B. Org. Lett. 2015, 17, 6118 10.1021/acs.orglett.5b03142
62. Gandeepan, P.; Rajamalli, P.; Cheng, C.-H. Angew. Chem., Int. Ed. 2016, 55, 4308 10.1002/anie.201512018
63. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087 10.1055/s-0029-1217131
64. Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 2013, 19 10.1002/ejoc.201200914
65. Yoshikai, N. Yuki Gosei Kagaku Kyokaishi 2014, 72, 1198 10.5059/yukigoseikyokaishi.72.1198
66. Yu, D.-G.; Gensch, T.; de Azambuja, F.; Vásquez-Céspedes, S.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17722 10.1021/ja511011m
67. Moselage, M.; Sauermann, N.; Koeller, J.; Liu, W.; Gelman, D.; Ackermann, L. Synlett 2015, 26, 1596 10.1055/s-0034-1379927
68. Gensch, T.; Vásquez-Céspedes, S.; Yu, D.-G.; Glorius, F. Org. Lett. 2015, 17, 3714 10.1021/acs.orglett.5b01701
69. Suzuki, Y.; Sun, B.; Sakata, K.; Yoshino, T.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2015, 54, 9944 10.1002/anie.201503704
70. III-catalyzed conditions with a stoichiometric oxidant, the β-hydride elimination pathway is dominant: Shi, Z.; Boultadakis-Arapinis, M.; Glorius, F. Chem. Commun. 2013, 49, 6489 10.1039/c3cc43903h
71. Kumar, G. S.; Kapur, M. Org. Lett. 2016, 18, 1112 10.1021/acs.orglett.6b00217
72. Guo, H.-M.; Jiang, L.-L.; Niu, H.-Y.; Rao, W.-H.; Liang, L.; Mao, R.-Z.; Li, D.-Y.; Qu, G.-R. Org. Lett. 2011, 13, 2008 10.1021/ol200405w
73. Guo, H.-M.; Rao, W.-H.; Niu, H.-Y.; Jiang, L.-L.; Meng, G.; Jin, J.-J.; Yang, X.-N.; Qu, G.-R. Chem. Commun. 2011, 47, 5608 10.1039/c1cc11135c
74. Lakshman, M. K.; Deb, A. C.; Chamala, R. R.; Pradhan, P.; Pratap, R. Angew. Chem., Int. Ed. 2011, 50, 11400 10.1002/anie.201104035
75. Chamala, R. R.; Parrish, D.; Pradhan, P.; Lakshman, M. K. J. Org. Chem. 2013, 78, 7423 10.1021/jo4008282
76. Kim, H. J.; Ajitha, M. J.; Lee, Y.; Ryu, J.; Kim, J.; Lee, Y.; Jung, Y.; Chang, S. J. Am. Chem. Soc. 2014, 136, 1132 10.1021/ja4118472
77. Patel, P.; Chang, S. ACS Catal. 2015, 5, 853 10.1021/cs501860b
78. Pawar, A. B.; Chang, S. Org. Lett. 2015, 17, 660 10.1021/ol503680d
79. Liang, Y.; Liang, Y.-F.; Tang, C.; Yuan, Y.; Jiao, N. Chem.-Eur. J. 2015, 21, 16395 10.1002/chem.201503533
80. Wang, S.; Hou, J.-T.; Feng, M.-L.; Zhang, X.-Z.; Chen, S.-Y.; Yu, X.-Q. Chem. Commun. 2016, 52, 2709 10.1039/C5CC09707J
81. Pawar, A. B.; Lade, D. M. Org. Biomol. Chem. 2016, 14, 3275 10.1039/C5OB02640G
82. Hocek, M.; Holý, A.; Votruba, I.; Dvořáková, H. J. Med. Chem. 2000, 43, 1817 10.1021/jm991167+
83. Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, B. J. Med. Chem. 2002, 45, 1383 10.1021/jm0110284
84. Bakkestuen, A. K.; Gundersen, L.-L.; Utenova, B. T. J. Med. Chem. 2005, 48, 2710 10.1021/jm0408924
85. Hocek, M.; Nauš, P.; Pohl, R.; Votruba, I.; Furman, P. A.; Tharnish, P. M.; Otto, M. J. J. Med. Chem. 2005, 48, 5869 10.1021/jm050335x
86. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118 10.1246/cl.2010.1118
87. Ackermann, L. Chem. Rev. 2011, 111, 1315 and references therein 10.1021/cr100412j
88. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815 10.1016/S0040-4039(01)91316-4
89. Balasubramaniam, S.; Aidhen, I. S. Synthesis 2008, 2008, 3707 and references therein 10.1055/s-0028-1083226
90. Yang, F.; Ackermann, L. Org. Lett. 2013, 15, 718 10.1021/ol303520h
91. Wang, Y.; Li, C.; Li, Y.; Yin, F.; Wang, X.-S. Adv. Synth. Catal. 2013, 355, 1724 10.1002/adsc.201300174
92. Davis, T. A.; Hyster, T. K.; Rovis, T. Angew. Chem., Int. Ed. 2013, 52, 14181 10.1002/anie.201307631
93. Wang, Y.; Zhou, K.; Lan, Q.; Wang, X.-S. Org. Biomol. Chem. 2015, 13, 353 10.1039/C4OB02039A
94. Walters, A. J. C.; Troeppner, O.; Ivanović-Burmazović, I.; Tejel, C.; del Río, M. P.; de Bruin, B. Angew. Chem., Int. Ed. 2012, 51, 5157 10.1002/anie.201200069
95. Gumrukcu, Y.; de Bruin, B.; Reek, J. N. H. Chem.-Eur. J. 2014, 20, 10905 10.1002/chem.201404026