Iron-Catalyzed Acylation-Oxygenation of Terminal Alkenes for the Synthesis of Dihydrofurans Bearing a Quaternary Carbon

Journal of Organic Chemistry

Volumn 80, Issue 1, 2015, Pages 698-704

  Lv, Leiyang ^a   Lu, Shenglin ^a   Guo, Qiaoxia ^b   Shen, Baojian ^b   Li, Zhiping ^a,b  

^a RENMIN UNIVERSITY OF CHINA   (China)

^b CHINA UNIVERSITY OF PETROLEUM   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CATALYSIS; HYDROCARBONS; OXYGENATION;

ACYL RADICALS; DIHYDROFURANS; FUNCTIONALIZED; QUATERNARY CARBON; TERMINAL ALKENES;

IRON COMPOUNDS;

2,3 DIHYDROFURAN DERIVATIVE; ALDEHYDE; ALKENE; CARBON; CARBONYL DERIVATIVE; FERROUS CHLORIDE; FURAN DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CATALYSIS; CATALYST; CONTROLLED STUDY; CYCLIZATION; OXIDATION; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 84924404596     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502535k     Document Type: Article

References (90)

1. Sumino, S.; Fusano, A.; Fukuyama, T.; Ryu, I. Acc. Chem. Res. 2014, 47, 1563
2. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1
3. Franke, R.; Selent, D.; Borner, A. Chem. Rev. 2012, 112, 5675
4. Liu, Q.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 10788
5. Brennfuhrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114
6. Gabriele, B.; Salerno, G.; Costa, M. Top. Organomet. Chem. 2006, 18, 239
7. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368
8. Kiss, G. Chem. Rev. 2001, 101, 3435
9. Wu, L.; Liu, Q.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 6310
10. Fujihara, T.; Iwai, T.; Terao, J.; Tsuji, Y. Synlett 2010, 2537
11. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202
12. Willis, M. C. Chem. Rev. 2010, 110, 725
13. Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869
14. Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580
15. Chudasama, V.; Fitzmaurice, R. J.; Caddick, S. Nat. Chem. 2010, 2, 529
16. Recupero, F.; Punta, C. Chem. Rev. 2007, 107, 3800
17. Schiesser, C. H.; Wille, U.; Matsubara, H.; Ryu, I. Acc. Chem. Res. 2007, 40, 303
18. Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794
19. Kim, S. Adv. Synth. Catal. 2004, 346, 19
20. Beccalli, E. M.; Broggini, G.; Gazzola, S.; Mazza, A. Org. Biomol. Chem. 2014, 12, 6767
21. Kanai, M.; Shimizu, Y. Tetrahedron Lett. 2014, 55, 3727
22. Zeng, X. Chem. Rev. 2013, 113, 6864
23. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464
24. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981
25. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
26. Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009
27. Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083
28. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
29. Minatti, A.; Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142
30. Yang, X.-H.; Wei, W.-T.; Li, H.-B.; Song, R.-J.; Li, J.-H. Chem. Commun. 2014, 50, 12867
31. Mai, W.-P.; Sun, G.-C.; Wang, J.-T.; Song, G.; Mao, P.; Yang, L.-R.; Yuan, J.-W.; Xiao, Y.-M.; Qu, L.-B. J. Org. Chem. 2014, 79, 8094
32. Fusano, A.; Sumino, S.; Fukuyama, T.; Ryu, I. Org. Lett. 2011, 13, 2114
33. Taniguchi, T.; Sugiura, Y.; Zaimoku, H.; Ishibashi, H. Angew. Chem., Int. Ed. 2010, 49, 10154
34. Cernak, T. A.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 3124
35. Uenoyama, Y.; Tsukida, M.; Doi, T.; Ryu, I.; Studer, A. Org. Lett. 2005, 7, 2985
36. Miura, K.; Tojino, M.; Fujisawa, N.; Hosomi, A.; Ryu, I. Angew. Chem., Int. Ed. 2004, 43, 2423
37. Ryu, I.; Kreimerman, S.; Araki, F.; Nishitani, S.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2002, 124, 3812
38. Niu, B.; Xu, L.; Xie, P.; Wang, M.; Zhao, W.; Pittman, C. U.; Zhou, A. ACS Comb. Sci. 2014, 16, 454
39. Luo, J.-Y.; Hua, H.-L.; Chen, Z.-S.; Zhou, Z.-Z.; Yang, Y.-F.; Zhou, P.-X.; He, Y.-T.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2014, 50, 1564
40. Wang, J.; Liu, C.; Yuan, J.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 2256
41. Zhou, M.-B.; Song, R.-J.; Ouyang, X.-H.; Liu, Y.; Wei, W.-T.; Deng, G.-B.; Li, J.-H. Chem. Sci. 2013, 4, 2690
42. Shi, Z.; Schrcder, N.; Glorious, F. Angew. Chem., Int. Ed. 2012, 51, 8092
43. Kilroy, T. G.; O'Sullivan, T. P.; Guiry, P. J. Eur. J. Org. Chem. 2005, 4929
44. Hou, X.-L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. Prog. Heterocycl. Chem. 2005, 17, 142
45. Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407
46. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217
47. Merrit, A. T.; Ley, S. V. Nat. Prod. Rep. 1992, 9, 243
48. Zhu, F.-L.; Wang, Y.-H.; Zhang, D.-Y.; Xu, J.; Hu, X.-P. Angew. Chem., Int. Ed. 2014, 53, 10223
49. Nakano, T.; Miyazaki, K.; Kamimura, A. J. Org. Chem. 2014, 79, 8103
50. Chagarovsky, A. O.; Budynina, E. M.; Ivanova, O. A.; Villemson, E. V.; Rybakov, V. B.; Trushkov, I. V.; Melnikov, M. Y. Org. Lett. 2014, 16, 2830
51. Li, M.; Lin, S.; Dong, Z.; Zhang, X.; Liang, F.; Zhang, J. Org. Lett. 2013, 15, 3978
52. Zhou, J.-L.; Wang, L.-J.; Xu, H.; Sun, X.-L.; Tang, Y. ACS Catal. 2013, 3, 685
53. Dou, X.; Zhong, F.; Lu, Y. Chem.-Eur. J. 2012, 18, 13945
54. Calter, M. A.; Korotkov, A. Org. Lett. 2011, 13, 6328
55. Zhong, C.; Liao, T.; Tuguldur, O.; Shi, X. Org. Lett. 2010, 12, 2064
56. Rueping, M.; Parra, A.; Uria, U.; Besselievre, F.; Merino, E. Org. Lett. 2010, 12, 5680
57. Zheng, J.-C.; Zhu, C.-Y.; Sun, X.-L.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2008, 73, 6909
58. Zhang, R.; Liang, Y.; Zhou, G.; Wang, K.; Dong, D. J. Org. Chem. 2008, 73, 8089
59. Son, S.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 1046
60. Alcaide, A.; Almendrous, P.; Campo, T. M. Angew. Chem., Int. Ed. 2006, 45, 4501
61. Xia, W.; Yang, C.; Patrick, B. O.; Scheffer, J. R.; Scott, C. J. Am. Chem. Soc. 2005, 127, 2725
62. Calter, M. A.; Phillips, R. M.; Flaschenriem, C. J. Am. Chem. Soc. 2005, 127, 14566
63. Ma, S.; Lu, L.; Zhang, J. L. J. Am. Chem. Soc. 2004, 126, 9645
64. Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095
65. Davies, H. M.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641
66. Naveen, T.; Kancherla, R.; Maiti, D. Org. Lett. 2014, 16, 5446
67. Ye, Y.; Wang, L.; Fan, R. J. Org. Chem. 2010, 75, 1760
68. Snider, B. B. Tetrahedron 2009, 65, 10738
69. Wang, G.-W.; Dong, Y.-W; Wu, P.; Yuan, T.-T.; Shen, Y.-B. J. Org. Chem. 2008, 73, 7088
70. Zhao, Y.; Jiang, X.; Yeung, Y.-Y. Angew. Chem., Int. Ed. 2013, 52, 8597
71. Lv, L.; Shen, B.; Li, Z. Angew. Chem., Int. Ed. 2014, 53, 4164
72. Jia, F.; Liu, K.; Xi, H.; Lu, S.; Li, Z. Tetrahedron Lett. 2013, 54, 6337
73. Liu, K.; Li, Y.; Liu, W.; Zheng, X.; Zong, Z.; Li, Z. Chem.-Asian. J. 2013, 8, 359
74. Liu, K.; Li, Y.; Zheng, X.; Liu, W.; Li, Z. Tetrahedron 2012, 68, 10333
75. Liu, W.; Li, Y.; Liu, K.; Li, Z. J. Am. Chem. Soc. 2011, 133, 10756
76. Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194
77. Gopalaiah, K. Chem. Rev. 2013, 113, 3248
78. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
79. Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
80. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
81. Plietker, B., Ed. Iron Catalysis in Organic Chemistry: Reactions and Applications; Wiley-VCH: Weinheim, Germany, 2008.
82. Moteki, S. A.; Usui, A.; Selvakumar, S.; Zhang, T.; Maruoka, K. Angew. Chem., Int. Ed. 2014, 53, 11060
83. Watanabe, E.; Kaiho, A.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 11744
84. Jensen, C. M.; Lindsay, K. B.; Taaning, R. H.; Karaffa, J.; Hansen, A. M.; Skrydstrup, T. J. Am. Chem. Soc. 2005, 127, 6544
85. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991
86. Liu, D.; Tang, S.; Yi, H.; Liu, C.; Qi, X.; Lan, Y.; Lei, A. Chem.-Eur. J. 2014, 20, 15605
87. Jiang, H.; Cheng, Y.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 4884
88. Cui, X.; Xu, X.; Wojtas, L.; Kim, M. M.; Zhang, X. P. J. Am. Chem. Soc. 2012, 134, 19981
89. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th edition; Butterworth-Heinemann, Linacre House, Jordan Hill: Oxford, 1997; pp 140.
90. Hok, S.; Schore, N. E. J. Org. Chem. 2006, 71, 1736