Mild and Efficient Ir(III)-Catalyzed Direct C-H Alkynylation of N-Phenoxyacetamides with Terminal Alkyne

ACS Catalysis

Volumn 5, Issue 11, 2015, Pages 6999-7003

  Zhou, Jie ^a   Shi, Jingjing ^a   Qi, Zisong ^b   Li, Xingwei ^b   Xu, H Eric ^a,c   Yi, Wei ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^c VAN ANDEL RESEARCH INSTITUTE   (United States)

Author keywords

C H alkynylation; Ir(III); N phenoxyacetamides; reaction mechanism; TIPS acetylene

Indexed keywords

ACETYLENE; CATALYSIS; CHEMICAL REACTIONS; LIGHTING;

ALKYNYLATIONS; DIRECTING GROUPS; MECHANISTIC STUDIES; MILD REACTION CONDITIONS; REACTION MECHANISM; SYNTHETIC APPLICATION; TERMINAL ALKYNE;

IRIDIUM;

EID: 84946811450     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b01571     Document Type: Article

References (109)

1. Diederich, F.; Stang, P. J.; Acetylene Chemistry: Chemistry, Biology and Material Science; Wiley-VCH: Weinheim, 2005.
2. Furstner, A.; Davies, P. W. Chem. Commun. 2005, 2307-2320 10.1039/b419143a
3. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem.; Int. Ed. 2001, 40, 2004-2021 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
4. Finn, M. G.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1231-1232 10.1039/c003740k
5. Brand, J. P.; Waser, J. Chem. Soc. Rev. 2012, 41, 4165-4179 10.1039/c2cs35034c
6. Chinchilla, R.; Nájera, C. Chem. Rev. 2014, 114, 1783-1826 10.1021/cr400133p
7. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem.; Int. Ed. 2001, 40, 2004-2021 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
8. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49 10.1016/S0022-328X(02)01158-0
9. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017 10.1021/cr020377i
10. King, A. O.; Yasuda, N. Top. Organomet. Chem. 2004, 6, 205-245 10.1007/b94551
11. Doucet, H.; Hierso, J. C. Angew. Chem.; Int. Ed. 2007, 46, 834-871 10.1002/anie.200602761
12. Plenio, H. Angew. Chem.; Int. Ed. 2008, 47, 6954-6956 10.1002/anie.200802270
13. Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084-5121 10.1039/c1cs15071e
14. Dudnik, A. S.; Gevorgyan, V. Angew. Chem.; Int. Ed. 2010, 49, 2096-2098 10.1002/anie.200906755
15. Kobayashi, K.; Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2002, 124, 8528-8529 10.1021/ja026108r
16. Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156-4159 10.1021/ol901684h
17. Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2010, 75, 1764-1766 10.1021/jo9025622
18. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250-3252 10.1021/ol901049r
19. Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742-7743 10.1021/ja072718l
20. Kim, S. H.; Chang, S. Org. Lett. 2010, 12, 1868-1871 10.1021/ol100488v
21. Brand, J. P.; Waser, J. Angew. Chem.; Int. Ed. 2010, 49, 7304-7307 10.1002/anie.201003179
22. Brand, J. P.; Chevalley, C.; Scopelliti, R.; Waser, J. Chem.-Eur. J. 2012, 18, 5655-5666 10.1002/chem.201200200
23. Brand, J. P.; Waser, J. Org. Lett. 2012, 14, 744-747 10.1021/ol203289v
24. Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330-14333 10.1021/ja306638s
25. Ano, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2012, 14, 354-357 10.1021/ol203100u
26. Feng, C.; Loh, T.-P. Angew. Chem.; Int. Ed. 2014, 53, 2722-2726 10.1002/anie.201309198
27. Collins, K. D.; Lied, F.; Glorius, F. Chem. Commun. 2014, 50, 4459-4461 10.1039/c4cc01141d
28. Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780-4787 10.1021/ja501910e
29. Wei, Y.; Zhao, H.; Kan, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522-2523 10.1021/ja910461e
30. Matsuyama, N.; Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2358-2361 10.1021/ol100699g
31. de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512-1513 10.1021/ja909726h
32. Yang, L.; Zhao, L.; Li, C. J. Chem. Commun. 2010, 46, 4184-4186 10.1039/c0cc00014k
33. Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474-1477 10.1021/ol200154s
34. Kim, S. H.; Park, S. H.; Chang, S. Tetrahedron 2012, 68, 5162-5166 10.1016/j.tet.2012.04.003
35. Jie, X.; Shang, Y.; Hu, P.; Su, W. Angew. Chem.; Int. Ed. 2013, 52, 3630-3633 10.1002/anie.201210013
36. Dong, J.; Wang, F.; You, J. Org. Lett. 2014, 16, 2884-2887 10.1021/ol501023n
37. Shang, M.; Wang, H. L.; Sun, S. Z.; Dai, X.; Yu, J. Q. J. Am. Chem. Soc. 2014, 136, 11590-11593 10.1021/ja507704b
38. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651-3687 10.1039/c2cs15281a
39. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814-825 10.1021/ar200190g
40. Zhu, C.; Wang, R.; Falck, J. R. Chem.-Asian J. 2012, 7, 1502-1514 10.1002/asia.201200035
41. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem.; Int. Ed. 2012, 51, 10236-10254 10.1002/anie.201203269
42. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 4, 886-896 10.1039/C2SC21524A
43. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369-375 10.1038/nchem.1607
44. Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem. Commun. 2014, 50, 29-39 10.1039/C3CC47028H
45. Ackermann, L. Acc. Chem. Res. 2014, 47, 281-295 10.1021/ar3002798
46. Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443-1460 10.1002/adsc.201400197
47. Zhang, M.; Zhang, Y.; Jie, X.; Zhao, H.; Li, G.; Su, W. Org. Chem. Front. 2014, 1, 843-895 10.1039/C4QO00068D
48. Zhuo, C. X.; Zheng, C.; You, S. L. Acc. Chem. Res. 2014, 47, 2558-2573 10.1021/ar500167f
49. Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613-8661 10.1021/cr400628s
50. He, R.; Huang, Z. T.; Zheng, Q. Y.; Wang, C. Tetrahedron Lett. 2014, 55, 5705-5713 10.1016/j.tetlet.2014.08.077
51. Han, Y. F.; Jin, G. X. Chem. Soc. Rev. 2014, 43, 2799-2823 10.1039/c3cs60343a
52. Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007-2823 10.1021/acs.accounts.5b00077
53. Wang, D. H.; Wasa, M.; Giri, R.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 7190-7191 10.1021/ja801355s
54. Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 14058-14059 10.1021/ja807129e
55. Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888-13889 10.1021/ja902762a
56. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350-2353 10.1021/ja109676d
57. Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846-11848 10.1039/C1CC15248C
58. Zhang, X.; Chen, D.; Zhao, M.; Zhao, J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011, 353, 719-723 10.1002/adsc.201000887
59. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449-6457 10.1021/ja201143v
60. Kornhaaβ, C.; Li, J.; Ackermann, L. J. Org. Chem. 2012, 77, 9190-9198 10.1021/jo301768b
61. Wang, H.; Glorius, F. Angew. Chem.; Int. Ed. 2012, 51, 7318-7322 10.1002/anie.201201273
62. Hyster, T. K.; Knörr, K. L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500-503 10.1126/science.1226132
63. Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592-19595 10.1021/ja310153v
64. Ye, B.; Cramer, N. Science 2012, 338, 504-507 10.1126/science.1226938
65. Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364-5367 10.1021/ja402274g
66. Cui, S.; Zhang, Y.; Wang, D.; Wu, Q. Chem. Sci. 2013, 4, 3912-3916 10.1039/c3sc51777b
67. Huang, X.; Huang, J.; Du, C.; Zhang, X.; Song, F.; You, J. Angew. Chem.; Int. Ed. 2013, 52, 12970-12974 10.1002/anie.201307174
68. Sharma, U.; Park, Y.; Chang, S. J. Org. Chem. 2014, 79, 9899-9906 10.1021/jo501995c
69. Zhao, D.; Lied, F.; Glorius, F. Chem. Sci. 2014, 5, 2869-2873 10.1039/c4sc00628c
70. Yu, D. G.; de Azambuja, F.; Gensch, T.; Daniliuc, C. G.; Glorius, F. Angew. Chem.; Int. Ed. 2014, 53, 9650-9654 10.1002/anie.201403782
71. Zhang, X.; Qi, Z.; Li, X. Angew. Chem.; Int. Ed. 2014, 53, 10794-10798 10.1002/anie.201406747
72. Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 2735-2738 10.1021/ja412444d
73. Liu, Y. J.; Xu, H.; Kong, W. J.; Shang, M.; Dai, H. X.; Yu, J. Q. Nature 2014, 515, 389-393 10.1038/nature13885
74. Wang, X.; Tang, H.; Feng, H.; Li, Y.; Yang, Y.; Zhou, B. J. Org. Chem. 2015, 80, 6238-6249 10.1021/acs.joc.5b00684
75. Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem.; Int. Ed. 2013, 52, 12426-12429 10.1002/anie.201306098
76. Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294-5297 10.1021/ol402523x
77. Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625-16631 10.1021/ja408541c
78. Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem.; Int. Ed. 2013, 52, 5795-5798 10.1002/anie.201301742
79. Zheng, L.; Hua, R. Chem.-Eur. J. 2014, 20, 2352-2326 10.1002/chem.201304302
80. Muralirajan, K.; Cheng, C. H. Adv. Synth. Catal. 2014, 356, 1571-1576 10.1002/adsc.201400224
81. Zhang, Z.; Jiang, H.; Huang, Y. Org. Lett. 2014, 16, 5976-5979 10.1021/ol502998n
82. Sun, H.; Wang, C.; Yang, Y. F.; Chen, P.; Wu, Y. D.; Zhang, X.; Huang, Y. J. Org. Chem. 2014, 79, 11863-11872 10.1021/jo500807d
83. Zhou, B.; Yang, Y.; Tang, H.; Du, J.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 3900-3903 10.1021/ol501599j
84. Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew. Chem.; Int. Ed. 2013, 52, 6033-6037 10.1002/anie.201300881
85. Shen, Y.; Liu, G.; Zhou, Z.; Lu, X. Org. Lett. 2013, 15, 3366-3369 10.1021/ol4014188
86. Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem.; Int. Ed. 2014, 53, 1364-1367 10.1002/anie.201309650
87. Zhang, H.; Wang, K.; Wang, B.; Yi, H.; Hu, F.; Li, C.; Zhang, Y.; Wang, J. Angew. Chem.; Int. Ed. 2014, 53, 13234-13238 10.1002/anie.201408555
88. Duan, P.; Lan, X.; Chen, Y.; Qian, S. S.; Li, J. J.; Lu, L.; Lu, Y.; Chen, B.; Hong, M.; Zhao, J. Chem. Commun. 2014, 50, 12135-12138 10.1039/C4CC05485G
89. Chen, Y.; Wang, D.; Duan, P.; Ben, R.; Dai, L.; Shao, X.; Hong, M.; Zhao, J.; Huang, Y. Nat. Commun. 2014, 5, 4610-4618 10.1038/ncomms5610
90. Zhou, J.; Shi, J.; Liu, X.; Jia, J.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 5868-5871 10.1039/C5CC00354G
91. Dai, H. X.; Li, G.; Zhang, X. G.; Stepan, A. F.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 7567-7571 10.1021/ja400659s
92. Li, B.; Ma, J.; Liang, Y.; Wang, N.; Xu, S.; Song, H.; Wang, B. Eur. J. Org. Chem. 2013, 2013, 1950-1962 10.1002/ejoc.201201574
93. Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406-12409 10.1021/ja204924j
94. Simonetti, S. O.; Larghi, E. L.; Bracca, A. B.; Kaufman, T. S. Nat. Prod. Rep. 2013, 30, 941-969 10.1039/c3np70014c
95. Naik, R.; Harmalkar, D. S.; Xu, X.; Jang, K.; Lee, K. Eur. J. Med. Chem. 2015, 90, 379-393 10.1016/j.ejmech.2014.11.047
96. Nevagi, R. J.; Dighe, S. N.; Dighe, S. N. Eur. J. Med. Chem. 2015, 97, 561-581 10.1016/j.ejmech.2014.10.085
97. Austin, M. B.; Noel, J. P. Nat. Prod. Rep. 2003, 20, 79-110 10.1039/b100917f
98. Ahcene, B.; Xavier, R.; Jean, B.; Boumendjel, A.; Ronot, X.; Boutonnat, J. Curr. Drug Targets 2009, 10, 363-371 10.2174/138945009787846416
99. Kumar, D.; Kumar, M.; Kumar, A.; Singh, S. K. Mini-Rev. Med. Chem. 2013, 13, 2116-2133 10.2174/13895575113136660101
100. Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565-10569 10.1021/ja103776u
101. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449-6457 10.1021/ja201143v
102. Jones, W. D. Acc. Chem. Res. 2003, 36, 140-146 10.1021/ar020148i
103. Simmons, E. M.; Hartwig, J. F. Angew. Chem.; Int. Ed. 2012, 51, 3066-3072 10.1002/anie.201107334
104. Zhang, S. S.; Wu, J. Q.; Liu, X.; Wang, H. ACS Catal. 2015, 5, 210-214 10.1021/cs501601c
105. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345 10.1021/cr100412j
106. Wang, H.; Glorius, F. Angew. Chem.; Int. Ed. 2012, 51, 7318-7322 10.1002/anie.201201273
107. Gorelsky, S. I. Coord. Chem. Rev. 2013, 257, 153-164 10.1016/j.ccr.2012.06.016
108. Zheng, J.; You, S. L. Chem. Commun. 2014, 50, 8204-8207 10.1039/c4cc02822h
109. Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009, 28, 3492-3500 10.1021/om9000742