Synthetic journey towards transition metal-free arylations

Research on Chemical Intermediates

Volumn 41, Issue 11, 2015, Pages 8111-8146

  Roopan, Selvaraj Mohana ^a   Palaniraja, Jeyakannu ^a  

^a VIT UNIVERSITY   (India)

Author keywords

Arenes; Arylation; Cross coupling reaction; Organo catalyst; Transition metal catalyst

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; HEAVY METALS; MICROWAVE HEATING; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

ARENES; ARYLATIONS; CROSS COUPLING REACTIONS; ELECTRON-RICH ARENES; ORGANIC SYNTHESIS; PHOTOCHEMICAL REACTOR; SYNTHETIC PATHWAYS; TRANSITION METAL CATALYSTS;

TRANSITION METALS;

EID: 84944164384     PISSN: 09226168     EISSN: 15685675     Source Type: Journal    
DOI: 10.1007/s11164-014-1880-6     Document Type: Article

References (103)

1. G.P. McGlacken, L.M. Bateman, Chem. Soc. Rev. 38, 2447-2464 (2009)
2. I. Kondolff, H. Doucet, M. Santelli, Organometallics 25, 5219-5222 (2006)
3. V.P. Mehta, B. Punji, RSC. Adv. 3, 11957-11986 (2013)
4. J.H. Kirchhoff, M.R. Netherton, I.D. Hill, G.C. Fu, J. Am. Chem. Soc. 124, 13662-13663 (2002)
5. Q. Wu, L. Wang, Synthesis 13, 2007-2012 (2008)
6. B.P. Fors, S.L. Buchwald, J. Am. Chem. Soc. 132, 15914-15917 (2010)
7. P. Li, L. Wang, H. Li, Tetrahedron 61, 8633-8640 (2005)
8. N. Yoshikai, H. Matsuda, E. Nakamura, J. Am. Chem. Soc. 131, 9590-9599 (2009)
9. S.P. Mee, V. Lee, J.E. Baldwin, Angew. Chem. Int. Ed. 43, 1132-1136 (2004)
10. S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 73, 7380-7382 (2008)
11. J.Y. Lee, G.C. Fu, J. Am. Chem. Soc. 125, 5616-5617 (2003)
12. O. Baudoin, Chem. Soc. Rev. 40, 4902-4911 (2011)
13. Q.L. Xu, H. Gao, M. Yousufuddin, D.H. Ess, L. Kurti, Aerob. J. Am. Chem. Soc. 135, 14048-14051 (2013)
14. B. Pruger, G.E. Hofmeister, C.B. Jacobsen, D.G. Alberg, M. Nielsen, K.A. Jorgensen, Chem. Eur. J. 16, 3783-3790 (2010)
15. W. Liu, F.T.X. Wang, H. Yu, Y. Bi, Chem. Commun. 49, 2983-2985 (2013)
16. L. Liu, J. Hu, X.C. Wang, M.J. Zhong, Y. Li, S.D. Yang, Y.M. Liang, Tetrahedron 68, 5391-5395 (2012)
17. H. Gao, D.H. Ess, M. Yousufuddin, Y. Kurthi, J. Am. Chem. Soc. 135, 7086-7089 (2013)
18. F.F. Zhuo, W.W. Xie, Y.X. Yang, L. Zhang, P. Wang, R. Yuan, C.S. Da, J. Org. Chem. 78, 3243-3249 (2013)
19. Q. Chen, X.M. Jourdin, P. Knochel, J. Am. Chem. Soc. 135, 4958-4961 (2013)
20. T. Pirali, F. Zhang, A.H. Miller, J.L. Head, D. McAusland, M.F. Greaney, Angew. Chem. Int. Ed. 51, 1006-1009 (2012)
21. T. Truong, O. Daugulis, Org. Lett. 14, 5964-5967 (2012)
22. K. Mohanan, Y. Coquerel, J. Rodriguez, Org. Lett. 14, 4686-4689 (2012)
23. R.A. Dhokale, P.R. Thakare, S.B. Mhaske, Org. Lett. 14, 3994-3997 (2012)
24. P. Kwan, M.J. Brodie, Epilepsia. 45, 1141-1149 (2004)
25. W. Liu, H. Cao, H. Zhang, K.H. Chung, C. He, H. Wang, F.Y. Kwong, A. Lei, J. Am. Chem. Soc. 132, 16737-16740 (2010)
26. W.C. Chen, Y.C. Hsu, W.C. Shih, C.Y. Lee, W.H. Chuang, Y.F. Tsai, P.P.Y. Chen, T.G. Ong, Chem. Commun. 48, 6702-6704 (2012)
27. T.D. Bradshaw, A.D. Westwell, Curr. Med. Chem. 11, 1009-1021 (2004)
28. Y. Gao, Q. Song, G. Cheng, X. Cui, Org. Biomol. Chem. 12, 1044-1047 (2014)
29. C. Marti, E.M. Carreira, Eur. J. Org. Chem. 12, 2209-2219 (2003)
30. H. Lin, S.J. Danishefsky, Angew. Chem. Int. Ed. 42, 36-51 (2003)
31. A.H. Beckett, R.W. Daisley, J. Walker, Tetrahedron 24, 6093-6109 (1968)
32. C. Crestini, R.A. Saladino, Synth. Commun. 24, 2835 (1994)
33. E.J. Hennessy, S.L. Buchwald, J. Am. Chem. Soc. 125, 12084-12085 (2003)
34. Z.Z. Zhao, H.L. Hua, J.Y. Luo, Z.S. Chen, P.X. Zhou, X.Y. Liu, Y.M. Liang, Tetrahedron 69, 10030-10035 (2013)
35. M. Rueping, M. Leiendecker, A. Das, T. Poisson, Chem. Commun. 47, 10629-10631 (2011)
36. H. Zhao, J. Shen, J. Guo, R. Ye, H. Zeng, Chem. Commun. 49, 2323-2325 (2013)
37. C.L. Sun, H. Li, D.G. Yu, M. Yu, X. Zhou, X.Y. Lu, K. Huang, S.F. Zheng, B.J. Li, Z.J. Shi, Nat. Chem. 2, 1044-1049 (2010)
38. E. Shirakawa, K.I. Itoh, T. Higashino, T. Hayashi, J. Am. Chem. Soc. 132, 15537-15539 (2010)
39. Y.S. Ng, C.S. Chan, K.S. Chan, Tetrahedron Lett. 53, 3911-3914 (2012)
40. X. Song, A. Song, F. Zhang, H.X. Li, W. Wang, Nat. Commun. 2, 524 (2011)
41. R.I. McDonald, G. Liu, S.S. Stahl, Chem. Rev. 111, 2981-3019 (2011)
42. Y. Li, D. Song, M. Dong, J. Am. Chem. Soc. 130, 2962-2964 (2008)
43. R. Zhu, S.L. Buchwald, Angew. Chem. Int. Ed. 124, 1962-1965 (2012)
44. B. Zhoa, X. Peng, Y. Zhu, T.A. Ramirez, R.G. Cornwall, Y. Shi, J. Am. Chem. Soc. 133, 20890-20900 (2011)
45. M.F. Mastral, M. Perez, P.H. Bos, A. Rudolph, S.R. Harutyuayan, B.L. Feringa, Angew. Chem. Int. Ed. 124, 1958-1961 (2012)
46. L. Shi, X. Yang, Y. Wang, H. Yang, H. Fua, Adv. Synth. Catal. 356, 1021-1028 (2014)
47. K. Muniz, Angew. Chem. Int. Ed. 121, 9576-9588 (2009)
48. S.R. Chemler, Org. Biomol. Chem. 7, 3009-3019 (2009)
49. R. Samanta, L. Lategahnzab, A.P. Antonchick, Chem. Commun. 48, 3194-3196 (2012)
50. J. Wen, R.Y. Zhang, S.Y. Chen, J. Zhang, X.Q. Yu, J. Org. Chem. 77, 766-771 (2012)
51. Y. Wu, S.M. Wong, F. Mao, T.L. Chan, F.Y. Kwong, Org. Lett. 14, 5306-5309 (2012)
52. A. Beyer, J. Buendia, C. Bolm, Org. Lett. 14, 3948-3951 (2012)
53. F.P. Crisostomo, T. Martin, R. Carrillo, Angew. Chem. Int. Ed. 53, 2181-2185 (2014)
54. M. Hartmann, Y. Li, A. Studer, J. Am. Chem. Soc. 134, 16516-16519 (2012)
55. G. Pratsch, T. Wallaschkowski, M.R. Heinrich, Chem. Eur. J. 18, 11555-11559 (2012)
56. Y.Z. Chen, D.H. Wang, B. Chen, J.J. Zhong, C.H. Tung, L.Z. Wu, J. Org. Chem. 77, 6773-6777 (2012)
57. R.W. Fischer, F. Roehrscheid, in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn. (Wiley, Weinheim, 2002), Vol. 1, pp. 443-467
58. B.T. Guan, B. Wang, M. Nishiura, Z. Hou, Angew. Chem. Int. Ed. 52, 4418-4421 (2013)
59. H. Qrareya, S. Raviola, S. Protti, M. Fagnoni, A. Albini, J. Org. Chem. 78, 6016-6024 (2013)
60. C. Raviola, S. Protti, D. Ravelli, M. Mella, A. Albini, M. Fagnoni, J. Org. Chem. 77, 9094-9101 (2012)
61. X. Zheng, L. Yang, W. Du, A. Ding, H. Guo, Chem. Asian J. 9, 439-442 (2014)
62. S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 10, 4673-4676 (2008)
63. A. Iglesias, E.G. Perez, K. Muniz, Angew. Chem. Int. Ed. 49, 8109-8111 (2010)
64. A.C. Spivey, T. Fekner, S.E. Spey, H. Adams, J. Org. Chem. 64, 9430-9443 (1999)
65. F. Mori, N. Fukawa, K. Noguchi, K. Tanaka, Org. Lett. 13, 362-365 (2011)
66. H.J. Son, W.S. Han, K.R. Wee, D.H. Yoo, J.H. Lee, S.K. Kwon, J. Ko, S.O. Kang, Org. Lett. 10, 5401-5404 (2008)
67. D.P. Hari, P. Schroll, B. Konig, J. Am. Chem. Soc. 134, 2958-2961 (2012)
68. S.V. Ley, A.W. Thomas, Angew. Chem. Int. Ed. 42, 5400-5449 (2003)
69. R. Zhu, S.L. Buchwald, Angew. Chem. Int. Ed. 51, 1926-1929 (2012)
70. T.A.J. Vijay, K.N. Nandeesh, G.M. Raghavendra, K.S. Rangappa, K. Mantelingu, Tetrahedron Lett. 54, 6533-6537 (2013)
71. R. Wang, Z. Chen, L. Yue, W. Pan, J.J. Zhao, Tetrahedron Lett. 53, 4529-4531 (2012)
72. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 108, 3054-3131 (2008)
73. D.A. Evans, J.L. Katz, G.S. Peterson, T. Hintermann, J. Am. Chem. Soc. 123, 12411-12413 (2001)
74. H. Deng, J.K. Juan, T. Liu, T.K.W. Kuntz, M.L. Snapper, A.H. Hoyeyda, J. Am. Chem. Soc. 125, 9032-9034 (2003)
75. N. Jalalian, T.B. Petersen, B. Olofsson, Chem. Eur. J. 18, 14140-14149 (2012)
76. S. Yang, C. Wua, M. Ruan, Y. Yang, Y. Zhao, J. Nic, W. Yang, J. Xu, J. Tetrahedron Lett. 53, 4288-4292 (2012)
77. T.B. Peterson, R. Khan, B. Olofsson, Org. Lett. 13, 3462-3465 (2011)
78. R. Hili, A.K. Yudin, Nat. Chem. Biol. 2, 284-287 (2006)
79. A.S. Guram, R.A. Rennels, S.L. Buchwald, Angew. Chem. Int. Ed. 34, 1348-1350 (1995)
80. D.M.T. Chan, K.L. Monaco, R.P. Wang, M.P. Winteres, Tetrahedron Lett. 39, 2933-2936 (1998)
81. W.C.P. Tsang, M. Zheng, S.L. Buchwald, J. Am. Chem. Soc. 127, 14560-14561 (2005)
82. P. Gu, J. Sun, Y.K. Kang, M. Yi, X.Q. Li, P. Xue, R. Li, Org. Lett. 15, 1124-1127 (2013)
83. L. Zhu, L. Cheng, Y. Zhang, R. Xie, J. You, J. Org. Chem. 72, 2737-2743 (2007)
84. C. Wolf, S. Liu, X. Mei, A.T. August, M.D. Casimir, J. Org. Chem. 71, 3270-3273 (2006)
85. M.T. Barros, S.S. Dey, C.D. Maycock, Eur. J. Org. Chem. 4, 742-747 (2013)
86. R. Singh, B.K. Allam, D.S. Raghuvanshi, K.N. Singh, Tetrahedron 69, 1038-1042 (2013)
87. C. Chen, C. Chen, B. Li, J. Tao, J. Peng, Molecules 17, 12506-12520 (2012)
88. M.T. Barros, S.S. Dey, C.D. Maycock, P. Rodriquesb, Chem. Commun. 48, 10901-10903 (2012)
89. J.C. Haber, M.A. Lynch, S.L. Spring, A.D. Pechulis, J. Raker, Y. Wang, Tetrahedron Lett. 52, 5847-5850 (2011)
90. X. Huang, M. Patil, C. Fares, W. Thiel, N. Maulide, J. Am. Chem. Soc. 135, 7312-7323 (2013)
91. Y. Zou, E. Zhang, T. Xu, W. Wu, Y. Chen, C. Yuan, W. Weia, X. Zhangd, RSC Adv. 3, 6545-6552 (2013)
92. Y.P. Zhu, M.C. Liu, F.C. Jia, J.J. Yuan, Q.H. Gao, M. Lian, A.X. Wu, Org. Lett. 14, 3392-3395 (2012)
93. P. Ceccherelli, M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, J. Org. Chem. 60, 8412-8413 (1995)
94. X. Huang, A. Sun, J. Org. Chem. 65, 6561-6565 (2000)
95. A. Ogawa, Selenium and Tellurium in Organic Synthesis in Main Group Metals in Organic Synthesis (Wiley, Weinheim, 2004), Vol. 2, pp. 813-866
96. C.W. Nogueira, J.B. Rocha, Arch. Toxicol. 85, 1313-1359 (2011)
97. Y. Kobiki, S.I. Kawaguchi, T. Ohe, A. Ogawa, Beilstein J. Org. Chem. 9, 1141-1147 (2013)
98. A. Corma, H. Garcia, F.X. Llabre's i Xamena, Chem. Rev. 110, 4606-4655 (2010)
99. R. Kitaura, S. Kitagawa, Y. Kubota, T.C. Kobayashi, Y. Mita, K. Kindo, A. Matsuo, M. Kobayashi, H.C. Chang, T.C. Ozawa, M. Suzuki, M. Sakata, M. Takata, Science 20, 2358-2361 (2002)
100. S. Horike, M. Dinca, K. Tamaki, J.R. Long, J. Am. Chem. Soc. 130, 5854-5855 (2008)
101. H. Liu, Y. Liu, Y. Li, Z. Tang, H. Jiang, J. Phys. Chem. C 114, 13362-13369 (2010)
102. H. Liu, B. Yin, Z. Gao, Y. Li, H. Jiang, Chem. Commun. 48, 2033-2035 (2012)
103. S. Haldar, S. Mahato, C.K. Jana, Asian J. Org. Chem. 3, 44-47 (2014)