Pd-catalyzed oxidative coupling of arene C-H bonds with benzylic ethers as acyl equivalents

Journal of Organic Chemistry

Volumn 79, Issue 1, 2014, Pages 275-284

  Han, Sangil ^a   Sharma, Satyasheel ^a   Park, Jihye ^a   Kim, Mirim ^a   Shin, Youngmi ^a   Mishra, Neeraj Kumar ^a   Bae, Jong Jin ^b   Kwak, Jong Hwan ^a   Jung, Young Hoon ^a   Kim, In Su ^a  

^a Sungkyunkwan University   (South Korea)

^b Woosuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC ETHERS; C-H BOND; CATALYTIC ACYLATION; CH-BOND ACTIVATION; DIBENZYL ETHERS; DIRECTING GROUPS; OXIDATIVE COUPLINGS; PALLADIUM-CATALYZED;

ACYLATION; CATALYSIS; FUNCTIONAL GROUPS;

ETHERS;

BENZYLIC ETHER; ETHER DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; OXIDATIVE COUPLING;

CATALYSIS; ETHERS; HYDROGEN BONDING; OXIDATIVE COUPLING; PALLADIUM;

EID: 84891698563     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4024304     Document Type: Article

References (65)

1. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
2. Ackermann, L. Chem. Rev. 2011, 111, 1315
3. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
4. Wencel-Delord, J.; Dröge, T.; Kiu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
5. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
6. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
7. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170
8. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
9. Mousseau, J. J.; Charette, A. B. Acc. Chem. Res. 2013, 46, 412
10. Guobing, Y.; Xiangmei, W.; Minghua, Y. Org. Biomol. Chem. 2013, 11, 5588
11. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529
12. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
13. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
14. Scheuermann, C. J. Chem.-Asian J. 2010, 5, 436
15. Jia, X.; Zhang, S.; Wang, W.; Luo, F.; Cheng, J. Org. Lett. 2009, 11, 3120
16. Park, J.; Park, E.; Kim, A.; Lee, Y.; Chi, K.-W.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org. Lett. 2011, 13, 4390
17. Sharma, S.; Park, E.; Park, J.; Kim, I. S. Org. Lett. 2012, 14, 906
18. Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 332
19. Chan, C.-W.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 3926
20. Yang, Y.; Zhou, B.; Li, Y. Adv. Synth. Catal. 2012, 354, 2916
21. Sharma, S.; Kim, A.; Park, J.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Park, J. S.; Kim, I. S. Org. Biomol. Chem. 2013, 11, 7869
22. Xiao, F.; Shuai, Q.; Zhao, F.; Baslé, O.; Deng, G.; Li, C.-J. Org. Lett. 2011, 13, 1614
23. Park, J.; Kim, A.; Sharma, S.; Kim, M.; Park, E.; Jeon, Y.; Lee, Y.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org. Biomol. Chem. 2013, 11, 2766
24. Kim, M.; Sharma, S.; Park, J.; Kim, M.; Choi, Y.; Jeon, Y.; Kwak, J. H.; Kim, I. S. Tetrahedron 2013, 69, 6552
25. Sharma, S.; Kim, M.; Park, J.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Oh, J. S.; Lee, Y.; Kim, I. S. Eur. J. Org. Chem. 2013, 6656
26. Fang, P.; Li, M.; Ge, H. J. Am. Chem. Soc. 2010, 132, 11898
27. Li, M.; Ge, H. Org. Lett. 2010, 12, 3464
28. Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Lett. 2012, 14, 4358
29. Kim, M.; Park, J.; Sharma, S.; Kim, A.; Park, E.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Chem. Commun. 2013, 49, 925
30. Park, J.; Kim, M.; Sharma, S.; Park, E.; Kim, A.; Lee, S. H.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Chem. Commun. 2013, 49, 1654
31. Sharma, S.; Kim, A.; Park, E.; Park, J.; Kim, M.; Kwak, J. H.; Lee, S. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 667
32. Yu, L.; Li, P.; Wang, L. Chem. Commun. 2013, 49, 2368
33. Li, H.; Li, P.; Zhao, Q.; Wang, L. Chem. Commun. 2013, 49, 9170
34. Miao, J.; Ge, H. Org. Lett. 2013, 15, 2930
35. Guin, S.; Rout, S. K.; Banerjee, A.; Nandi, S.; Patel, B. K. Org. Lett. 2012, 14, 5294
36. Wu, Y.; Choy, P. Y.; Mao, F.; Kwong, F. Y. Chem. Commun. 2013, 49, 689
37. Zhou, W.; Li, H.; Wang, L. Org. Lett. 2012, 14, 4594
38. Lu, J.; Zhang, H.; Chen, X.; Liu, H.; Jiang, Y.; Fu, H. Adv. Synth. Catal. 2013, 355, 529
39. Zhang, Q.; Yang, F.; Wu, Y. Chem. Commun. 2013, 49, 6837
40. Wuts, P. G. M.; Green, T. W. Protective Groups in Organic Synthesis, 4 th ed.; Wiley & Sons: New York, 2007; pp 102-120.
41. Markees, D. G. J. Org. Chem. 1958, 23, 1490
42. Mayhoub, A. S.; Talukdar, A.; Cushman, M. J. Org. Chem. 2010, 75, 3507
43. Pradhan, P. P.; Bobbitt, J. M.; Bailey, W. F. J. Org. Chem. 2009, 74, 9524
44. Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 526
45. Nishiguchi, T.; Bougauchi, M. J. Org. Chem. 1989, 54, 3001
46. Lee-Ruff, E.; Ablenas, F. J. Can. J. Chem. 1989, 67, 699
47. Shen, Z.; Dai, J.; Xiong, J.; He, X.; Mo, W.; Hu, B.; Sun, N.; Hu, X. Adv. Synth. Catal. 2011, 353, 3031
48. Sun, C.-L.; Liu, N.; Li, B.-J.; Yu, D.-G.; Wang, Y.; Shi, Z.-J. Org. Lett. 2010, 12, 184
49. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462
50. Warren, J. M.; Mayer, J. M. J. Am. Chem. Soc. 2010, 132, 7784
51. Brutchey, R. L.; Drake, I. J.; Bell, A. T.; Tilley, T. D. Chem. Commun. 2005, 3736
52. Yi, C. S.; Kwon, K.-H.; Lee, D. W. Org. Lett. 2009, 11, 1567
53. Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96
54. Bordwell, F. G.; Cornforth, F. J. J. Org. Chem. 1978, 43, 1763
55. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050
56. Joo, J. M.; Touré, B. B.; Sames, D. J. Org. Chem. 2010, 75, 4911
57. Sun, H.-Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180
58. For a review of palladacycles, see: Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527
59. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991
60. Shi, Z.; Glorius, F. Chem. Sci. 2013, 4, 829
61. Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231
62. Neufeldt, S. R.; Sanford, M. S. Adv. Synth. Catal. 2012, 354, 3517
63. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177
64. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
65. Arnold, P. L.; Sanford, M. S.; Pearson, S. M. J. Am. Chem. Soc. 2009, 131, 13912