Ru-catalyzed ortho-oxidative alkenylation of 2-arylbenzo[d]thiazoles in aqueous solution of anionic surfactant sodium dodecylbenzenesulfonate (SDBS)

Tetrahedron

Volumn 73, Issue 5, 2017, Pages 594-603

  Ping, Yuanyuan ^a   Chen, Zhaobin ^a   Ding, Qiuping ^a   Zheng, Qiang ^a   Lin, Yuqing ^a   Peng, Yiyuan ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

2 arylbenzo d thiazoles; 2 arylthiazoles; Alkenylation; Aqueous; C H functionalization

Indexed keywords

(2,2') DIBUTYL 3,3' [2 (BENZO[D]THIAZOL 2 YL) 1,3 PHENYLENE]DIACRYLATE; (2,2') DIBUTYL3,3'[2 (BENZO[D]THIAZOL 2 YL) 5 METHOXY 1,3 PHENYLENE]DIACRYLATE; (2,2'DIBUTYL 3,3'[2 (6 METHYLBENZO[D]THIAZOL 2 YL) 1,3 PHENYLENE]DIACRYLATE; BUTYL 3 [2 (6 CHLOROBENZO[D]THIAZOL 2 YL) 3 FLUOROPHENYL]ACRYLATE; BUTYL 3 [2 (6 CHLOROBENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]ACRYLATE; BUTYL 3 [2 (6 CHLOROBENZO[D]THIAZOL 2 YL) 4 METHYLPHENYL]ACRYLATE; BUTYL 3 [2 (6 FLUOROBENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]ACRYLATE; BUTYL 3 [2 (6 FLUOROBENZO[D]THIAZOL 2 YL) 4 METHYLPHENYL]ACRYLATE; BUTYL 3 [2 (6 METHYLBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 CHLOROPHENYL]; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 FLUOROPHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 METHOXYPHENYL]; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 NITROPHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 4 CHLOROPHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 4 METHYLPHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 5 METHOXYPHENYL]ACRYLATE; BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [3 CHLORO 2 (6 FLUOROBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [3 CHLORO 2 (6 METHYLBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [3 FLUORO 2 (6 FLUOROBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [3 FLUORO 2 (6 METHYLBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL 3 [4 CHLORO 2 (6 METHYLBENZO[D]THIAZOL 2 YL)PHENYL]ACRYLATE; BUTYL [2 (BENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]; DODECYLBENZENESULFONATE SODIUM; ETHYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]ACRYLATE; METHYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]ACRYLATE; RUTHENIUM; TERT BUTYL 3 [2 (BENZO[D]THIAZOL 2 YL) 3 METHYLPHENYL]ACRYLATE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKENYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; COUPLING FACTOR; HUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 85008957127     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2016.12.050     Document Type: Article

References (123)

1. 1(a) Wang, K., Guengerich, F.P., Chem Res Toxicol, 25, 2012, 1740.
2. 1(b) Tan, B.S., Tiong, K.H., Muruhadas, A., et al. Mol Cancer Ther, 10, 2011, 1982.
3. 1(c) Rajashekhar, H., Ramesh, D., Chandarashekhar, C., Mahadevan, K.M., Vaidya, V.P., Indian J Heterocycl Chem, 18, 2009, 205.
4. 1(d) Aiello, S., Wells, G., Stone, E.L., et al. J Med Chem, 51, 2008, 5135.
5. 1(e) Kalgutkar, A.S., Gardner, I., Obach, R.S., et al. Curr Drug Metab, 6, 2005, 161.
6. 1(f) Hutchinson, I., Chua, M.S., Browne, H.L., et al. J Med Chem, 44, 2001, 1446.
7. 2(a) Rowland, L.K., McLean, L.S., Campbell, P., et al. Eileen Brantley AACR 106th Annual Meeting 2015, April 18-22, 2015.
8. 2(b) Coliva, A., Monterisi, C., Apollaro, A., et al. Appl Radiat Isot, 105, 2015, 66.
9. 2(c) Lanman, B.A., Cee, V.J., Cheruku, S.R., et al. ACS Med Chem Lett, 2, 2011, 102.
10. 2(d) Sun, Q., Wu, R., Cai, S., et al. J Med Chem, 54, 2011, 1126.
11. 2(e) Cellier, M., Fabrega, O.J., Fazackerley, E., et al. Bioorg Med Chem, 19, 2011, 2903.
12. 2(f) Kiyoshi, N., Masamichi, T., Makoto, A., PCT Int Appl. 2007 WO 2007091313 A1 20070816.
13. 2(g) Mortimer, C.G., Wells, G., Crochard, J.P., et al. J Med Chem, 49, 2006, 179.
14. Some selected reviews.
15. 3(a) Liu, J., Chen, G., Tan, Z., Adv Synth Catal, 358, 2016, 1174.
16. 3(b) Bag, S., Maiti, D., Synthesis, 48, 2016, 804.
17. 3(c) Yadav, M.R., Rit, R.K., Shankar, M., Sahoo, A.K., Asian J Org Chem, 4, 2015, 846.
18. 3(d) Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., Zhang, Y., Org Chem Front, 2, 2015, 1107.
19. 3(e) Zhang, F., Spring, D.R., Chem Soc Rev, 43, 2014, 6906.
20. 3(f) Rao, Y., Shan, G., Yang, X., Sci China Chem, 57, 2014, 930.
21. 3(g) Shi, G., Zhang, Y., Adv Synth Catal, 356, 2014, 1419.
22. 3(h) Li, Y., Wu, Y., Li, G.-S., Wang, X.-S., Adv Synth Catal, 356, 2014, 1412.
23. 3(i) Rossi, R., Bellina, F., Lessi, M., Manzini, C., Adv Synth Catal, 356, 2014, 17.
24. 3(j) Zhang, M., Zhang, Y., Jie, X., Zhao, H., Li, G., Su, W., Org Chem Front, 1, 2014, 843.
25. 3(k) Zhang, W., Zhang, J., Liu, Y., Chin J Org Chem, 34, 2014, 36.
26. 3(l) Li, B.-J., Shi, Z.-J., Chem Soc Rev, 41, 2012, 5588.
27. For selected recent examples, see.
28. 4(a) Ding, Q., Ji, H., Wang, D., Lin, Y., Yu, W., Peng, Y.J., Organomet Chem, 711, 2012, 62.
29. 4(b) Choi, M., Park, J., Mishra, N.K., et al. Tetrahedron Lett, 56, 2015, 4678.
30. 4(c) Ding, Q., Ji, H., Nie, Z., Yang, Q., Peng, Y., J Organomet Chem, 739, 2013, 33.
31. 4(d) Ding, Q., Ye, C., Pu, S., Cao, B., Tetrahedron, 70, 2014, 409.
32. 4(e) Ding, Q., Zhou, X., Pu, S., Cao, B., Tetrahedron, 71, 2015, 2376.
33. 4(f) Zhou, X., Luo, P., Long, L., Ouyang, M., Sang, X., Ding, Q., Tetrahedron, 70, 2014, 6742.
34. 4(g) Ding, Q., Ji, H., Ye, C., et al. Tetrahedron, 69, 2013, 8661.
35. 4(h) Wang, J., Nie, Z., Li, Y., et al. J Chem Res, 37, 2013, 263.
36. 4(i) Banerjee, A., Santra, S.K., Guin, S., Rout, S.K., Patel, B.K., Eur J Org Chem, 7, 2013, 1367.
37. 4(j) Zheng, Y., Song, W.B., Zhang, S.W., Xuan, L.J., Tetrahedron, 71, 2015, 1574.
38. 4(k) Banerjee, A., Bera, A., Guin, S., Rout, S.K., Patel, B.K., Tetrahedron, 69, 2013, 2175.
39. 4(l) Seth, K., Nautiyal, M., Purohit, P., Parikh, N., Chakraborti, A.K., Chem Commun, 51, 2015, 191.
40. 4(m) Qiao, H.-J., Yang, F., Wang, S.-W., Leng, Y.-T., Wu, Y.-J., Tetrahedron, 71, 2015, 9258.
41. 4(n) Luo, P., Ding, Q., Ping, Y., Hu, J., Org Biomol Chem, 14, 2016, 2924.
42. 4(o) Ping, Y., Ding, Q., Chen, Z., Peng, Y., J Organomet Chem, 815–816, 2016, 59.
43. Some selected recent examples of Rh-catalyzed C–H bond alkenylation reaction.
44. 5(a) Liu, B., Li, R., Zhan, W., Wang, X., Ge, Z., Li, R., RSC Adv, 6, 2016, 48205.
45. 5(b) Borah, A.J., Yan, G., Wang, L., Eur J Org Chem, 21, 2015, 4782.
46. 5(c) Yang, X.-F., Hu, X.-H., Feng, C., Loh, T.-P., Chem Commun, 51, 2015, 2532.
47. 5(d) Unoh, Y., Hirano, K., Satoh, T., Miura, M., Org Lett, 17, 2015, 704.
48. 5(e) Zhang, L., Qiu, R., Xue, X., et al. Chem Commun, 50, 2014, 12385.
49. 5(f) Parthasarathy, K., Bolm, C., Chem Eur J, 20, 2014, 4896.
50. 5(g) Cai, S., Chen, C., Shao, P., Xi, C., Org Lett, 16, 2014, 3142.
51. 5(h) Vora, H.U., Silvestri, A.P., Engelin, C.J., Yu, J.-Q., Angew Chem Int Ed, 53, 2014, 2683.
52. 5(i) Mishra, N.K., Park, J., Sharma, S., et al. Chem Commun, 50, 2014, 2350.
53. 5(j) Hu, F., Xia, Y., Ye, F., et al. Angew Chem Int Ed, 53, 2014, 1364.
54. 5(k) Zhang, T., Wu, L., Li, X., Org Lett, 15, 2013, 6294.
55. 5(l) Iitsuka, T., Schaal, P., Hirano, K., Satoh, T., Bolm, C., Miura, M., J Org Chem, 78, 2013, 7216.
56. 5(m) Zhang, Q., Yu, H.-Z., Li, Y.-T., Liu, L., Huang, Y., Fu, Y., Dalton Trans, 42, 2013, 4175.
57. 5(n) Liu, B., Fan, Y., Gao, Y., Sun, C., Xu, C., Zhu, J., J Am Chem Soc, 135, 2013, 468.
58. 5(o) Wang, C., Chen, H., Wang, Z.F., Chen, J.A., Huang, Y., Angew Chem Int Ed, 51, 2012, 7242.
59. Some selected recent examples of Pd-catalyzed C–H bond alkenylation reaction.
60. 6(a) Kannaboina, P., Kumar, K.A., Das, P., Org Lett, 18, 2016, 900.
61. 6(b) Han, S.J., Kim, H.T., Joo, J.M., J Org Chem, 81, 2016, 689.
62. 6(c) Liu, P., Han, J., Wang, Q., et al. RSC Adv, 5, 2015, 60646.
63. 6(d) He, P., Tiana, Q., Kuang, C., Org Biomol Chem, 13, 2015, 7146.
64. 6(e) Hu, J., Guan, M., Han, J., Huang, Z.-B., Shi, D.-Q., Zhao, Y., J Org Chem, 80, 2015, 7896.
65. 6(f) Alfonso, G.-R., Eduardo, L., Carlos, C., Esteban, P.U., Ramón, G.-A., Juan, C.C., J Org Chem, 80, 2015, 3321.
66. 6(g) Muselli, M., Baudequin, C., Hoarau, C., Chem Commun, 51, 2015, 745.
67. 6(h) Cao, H., Lei, S., Liao, J., et al. RSC Adv, 4, 2014, 50137.
68. 6(i) Deb, A., Bag, S., Kancherla, R., Maiti, D., J Am Chem Soc, 136, 2014, 13602.
69. 6(j) Xie, W., Yang, J., Wang, B., Li, B., J Org Chem, 79, 2014, 8278.
70. 6(k) He, C.-Y., Qing, F.-L., Zhang, X., Tetrahedron Lett, 55, 2014, 2962.
71. 6(l) Mishra, N.K., Park, J., Sharma, S., et al. Chem Commun, 50, 2014, 2350.
72. 6(m) Lu, Z., Luo, F., Wang, L., J Org Chem, 78, 2013, 10894.
73. 6(n) Huang, Q., Song, Q., Cai, J., Adv Synth Catal, 355, 2013, 1512.
74. 6(o) Chan, L.Y., Kim, S., Ryu, T., Lee, P.H., Chem Commun, 49, 2013, 4682.
75. 6(p) Dai, H.-X., Li, G., Zhang, X.-G., Stepan, A.F., Yu, J.-Q., J Am Chem Soc, 135, 2013, 7567.
76. 6(q) Li, G., Leow, D., Wan, L., Yu, J.-Q., Angew Chem Int Ed, 52, 2013, 1245.
77. 6(r) Leow, D., Li, G., Mei, T.-S., Yu, J.-Q., Nature, 486, 2012, 518.
78. 7(a) Suzuki, C., Hirano, K., Satoh, T., Miura, M., Org Lett, 15, 2013, 3990.
79. 7(b) Hashimoto, Y., Ortloff, T., Hirano, K., Satoh, T., Bolm, C., Miura, M., Chem Lett, 41, 2012, 151.
80. 7(c) Hashimoto, Y., Ueyama, T., Fukutani, T., Hirano, K., Satoh, T., Miura, M., Chem Lett, 40, 2011, 1165.
81. 7(d) Ueyama, T., Mochida, S., Fukutani, T., Hirano, K., Satoh, T., Miura, M., Org Lett, 13, 2011, 706.
82. 8(a) Kumar, N.Y.P., Bechtoldt, A., Raghuvanshi, K., Ackermann, L., Angew Chem Int Ed, 55, 2016, 6929.
83. 8(b) Ma, W., Ackermann, L., Chem Eur J, 19, 2013, 13925.
84. 8(c) Kozhushkov, S.I., Ackermann, L., Chem Sci, 4, 2013, 886.
85. 8(d) Li, J., Kornhaaβ, C., Ackermann, L., Chem Commun, 48, 2012, 11343.
86. 8(e) Graczyk, K., Ma, W., Ackermann, L., Org Lett, 14, 2012, 4110.
87. 8(f) Ackermann, L., Wang, L., Wolfram, R., Lygin, A.V., Org Lett, 14, 2012, 728.
88. 8(g) Ackermann, L., Fenner, S., Org Lett, 13, 2011, 6548.
89. 8(h) Ackermann, L., Pospech, J., Org Lett, 13, 2011, 4153.
90. 9(a) Padala, K., Jeganmohan, M., Org Lett, 14, 2012, 1134.
91. 9(b) Padala, K., Jeganmohan, M., Org Lett, 13, 2011, 6144.
92. 10(a) Li, B., Devaraj, K., Darcel, C., Dixneuf, P.H., Green Chem, 14, 2012, 2706.
93. 10(b) Arockiam, P.B., Fischmeister, C., Bruneau, C., Dixneuf, P.H., Green Chem, 13, 2011, 3075.
94. Some selected recent examples of Ru-catalyzed C–H bond alkenylation reaction.
95. 11(a) Zhan, H., Zhao, L., Li, N., et al. RSC Adv, 4, 2014, 32013.
96. 11(b) Yadav, M.R., Rit, R.K., Shankar, M., Sahoo, A.K., J Org Chem, 79, 2014, 6123.
97. 11(c) Li, H., Xie, X., Wang, L., Chem Commun, 50, 2014, 4218.
98. 11(d) Zhang, L.-Q., Yang, S., Huang, X., You, J., Song, F., Chem Commun, 49, 2013, 8830.
99. 11(e) Li, B., Ma, J., Xie, W., Song, H., Xu, S., Wang, B., J Org Chem, 78, 2013, 9345.
100. 11(f) Chidipudi, S.R., Wieczysty, M.D., Khan, I., Lam, H.W., Org Lett, 15, 2013, 570.
101. 11(g) Lee, D.-H., Kwon, K.-H., Yi, C.S., J Am Chem Soc, 134, 2012, 7325.
102. 11(h) Zhao, P., Niu, R., Wang, F., Han, K., Li, X., Org Lett, 14, 2012, 4166.
103. 11(i) Li, B., Ma, J., Wang, N., Feng, H., Xu, S., Wang, B., Org Lett, 14, 2012, 736.
104. Some selected recent examples of Fe-catalyzed C–H bond alkenylation reaction.
105. 12(a) Yang, X.-H., Song, R.-J., Xie, Y.-X., Li, J.-H., ChemCatChem, 2016, 10.1002/cctc.201600019.
106. 12(b) Cavanagh, C.W., Aukland, M.H., Laurent, Q., Hennessy, A., Procter, D.J., Org Biomol Chem, 14, 2016, 5286.
107. 12(c) Dang, H.T., Lieu, T.N., Truong, T., Phan, N.T.S., J Mol Catal A Chem, 420, 2016, 237.
108. 12(d) Ma, Y., Zhang, D., Yan, Z., et al. Org Lett, 17, 2015, 2174.
109. 12(e) Wong, M.Y., Yamakawa, T., Yoshikai, N., Org Lett, 17, 2015, 442.
110. 12(f) Huang, Z., Jin, L., Feng, Y., Peng, P., Yi, H., Lei, A., Angew Chem Int Ed, 52, 2013, 7151.
111. 12(g) Zhao, J., Zhou, W., Han, J., Li, G., Pan, Y., Tetrahedron Lett, 54, 2013, 6507.
112. 12(h) Zhao, J., Fang, H., Han, J., Beilstein J Org Chem, 9, 2013, 1718.
113. 12(i) Yang, H., Yan, H., Sun, P., et al. Green Chem, 15, 2013, 976.
114. 12(j) Qian, B., Xie, P., Xie, Y., Org Lett, 13, 2011, 2580.
115. 13(a) Butler, R.N., Coyne, A.G., Chem Rev, 110, 2010, 6302.
116. 13(b) Pan, C., Wang, Z., Coord Chem Rev, 252, 2008, 736.
117. 13(c) Li, C.-J., Chen, L., Chem Soc Rev, 35, 2006, 68.
118. 13(d) Li, C.-J., Chem Rev, 105, 2005, 3095.
119. 13(e) Kobayashi, S., Manabe, K., Accounts Chem Res, 35, 2002, 209.
120. 13(f) Lindström, U.M., Chem Rev, 102, 2002, 2751.
121. 14 Ding, Q., Liu, T., Zheng, Q., Zhang, Y., Long, L., Peng, Y., RSC Adv, 4, 2014, 51309.
122. 15(a) Peng, Y., Liu, J., Lei, X., Yin, Z., Green Chem, 12, 2010, 1072.
123. 15(b) Ding, Q., Cao, B., Liu, X., Zong, Z., Peng, Y., Green Chem, 12, 2010, 1607.