Chinese Journal of Organic Chemistry >
Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates
Received date: 2021-06-15
Revised date: 2021-07-21
Online published: 2021-08-19
Supported by
Department Education Science and Technology Research Project of Jiangxi Province(GJJ190619); Department Education Science and Technology Research Project of Jiangxi Province(GJJ201143); PhD Research Startup Foundation of Jiangxi Science & Technology Normal University(2019BSQD016)
A simple and mild copper-catalyzed sulfonylation of naphthalen-1-amine with sodium and lithium sulfinates is reported. In the presence of iodine as oxidant a highly site-selective C—H functionalization at the C(4) position took place. The reaction proceeded readily mild conditions and various sulfones were synthesized in moderate to high yields.
Key words: copper-catalyzed; sulfonylation; remote C—H functionalization
Xiang Zhou , Rujian Yu , Jiantao Wang , Xiangwen Liao , Yanshi Xiong . Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4370 -4377 . DOI: 10.6023/cjoc202106030
[1] | (a) Patai, S.; Rappoport, C. Z.; Stirling, J. M. The Chemistry of Sulfones and Sulfoxides, Wiley, New York, 1988. |
[1] | (b) Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993. |
[2] | La Regina, G.; Coluccia, A.; Brancale, A.; Piscitelli, F.; Gatti, V.; Maga, G.; Samuele, A.; Pannecouque, C.; Schols, D.; Balzarini, J.; Novellino, E.; Silvestri, R. J. Med. Chem. 2011, 54, 1587. |
[3] | Ivachtchenko, A. V.; Golovina, E. S.; Kadieva, M. G.; Kysil, V. M.; Mitkin, O. D.; Tkachenko, S. E.; Okun, I. M. J. Med. Chem. 2011, 54, 8161. |
[4] | (a) Catarinella, M.; Gruner, T.; Strittmatter, T.; Marx, A.; Mayer, T. U. Angew. Chem., Int. Ed. 2009, 48, 9072. |
[4] | (b) Lu, Q.; Zhang, J.; Wei, F.; Qi, Y.; Wang, H.; Liu, Z.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 7156. |
[4] | (c) Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481. |
[4] | (d) Reddy, M. A.; Reddy, P. S.; Sreedhar, B. Adv. Synth. Catal. 2010, 352, 1861. |
[4] | (e) Fang, X.; Wang, W.; Yang, X.-Y.; Wu, F.-H. Chin. J. Org. Chem. 2021, 41, 412. (in Chinese) |
[4] | (方向, 王旺, 杨雪艳, 吴范宏, 有机化学, 2021, 41, 412.) |
[5] | (a) Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144. |
[5] | (b) Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao, Y. R.; Li, Y. Y.; He, N. N.; Guo, C.C. J. Org. Chem. 2014, 79, 7372. |
[5] | (c) Li, J.-M.; Weng, J.; Lu, G.; Chan, A. S. C. Tetrahedron Lett. 2016, 57, 212. |
[5] | (d) Liang, S.; Manolikakes, G. Adv. Synth. Catal. 2016, 358, 2371. |
[5] | (e) Liu, X.; Chen, X.; Mohr, J. T. Org. Lett. 2015, 17, 3572. |
[5] | (f) Qiao, H.; Sun, S.; Yang, F.; Zhu, Y.; Zhu, W.; Dong, Y.; Wu, Y.; Kong, X.; Jiang, L.; Wu, Y. Org. Lett. 2015, 17, 6086. |
[5] | (g) Rao, W. H.; Shi, B. F. Org. Lett. 2015, 17, 2784. |
[5] | (h) Rokade, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 8110. |
[5] | (i) Liu, D.; Mei, T.-S. Chin. J. Org. Chem. 2019, 39, 3600. (in Chinese) |
[5] | (刘冬, 梅天胜, 有机化学, 2019, 39, 3600.) |
[6] | (a) Liu, N. M.; Liang, S.; Manolikakes, G. Synthesis 2016, 48, 1939. |
[6] | (b) Shen, C.; Zhang, P. F.; Sun, Q.; Bai, S. Q.; Hor, T. S. A.; Liu, X. G. Chem. Soc. Rev. 2015, 44, 291. |
[6] | (c) Shaaban, S.; Liang, S.; Liu, N. W.; Manolikakes, G. Org. Biomol. Chem. 2017, 15, 1947. |
[7] | (a) Zhao, X. D.; Dimitrijevic, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466. |
[7] | (b) Liu, J. D.; Yu, L.; Zhuang, S. B.; Gui, Q. W.; Chen, X.; Wang, W. D.; Tan, Z. Chem. Commun. 2015, 51, 6418. |
[7] | (c) Liang, H. W.; Jiang, K.; Ding, W.; Yuan, Y.; Shuai, L.; Chen, Y. C.; Wei, Y. Chem. Commun. 2015, 51, 16928. |
[7] | (g) Xia, C. C.; Wang, K.; Xu, J.; Wei, Z. J.; Shen, C.; Duan, G. Y.; Zhu, Q.; Zhang, P. F. RSC Adv. 2016, 6, 37173. |
[8] | (a) Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082. |
[8] | (b) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651. |
[8] | (c) Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208. |
[8] | (d) Yang, L.; Huang, H. M. Chem. Rev. 2015, 115, 3468. |
[8] | (e) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. |
[8] | (f) Ackermann, L. Chem. Rev. 2011, 111,1315. |
[8] | (g) Shen, C.; Zhang, P. F.; Sun, Q.; Bai, S. Q.; Hor, T. S. A.; Liu, X. G. Chem. Soc. Rev. 2015, 44, 291. |
[8] | (h) Wang, X.-Y.; Gao, J.-Q.; Xu, X.-T.; Fang, P.; Mei, T.-S. Chin. J. Org. Chem. 2021, 41, 384. (in Chinese) |
[8] | (王向阳, 高君青, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 384.) |
[9] | For selected examples containing naphthalene derivatives as substrates in C-H activation of arenes, see: (a) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K.. J. Am. Chem. Soc. 2008, 130, 16474. |
[9] | (b) Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242. |
[9] | (c) Li, Q.; Zhang, S.-Y.; He, G.; Ai, Z.; Nack, W. A.; Chen, G. Org. Lett. 2014, 16, 1764. |
[9] | (d) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105. |
[9] | (e) Lee, D.; Chang, S. Chem.-Eur. J. 2015, 21, 5364. |
[9] | (f) Kondrashov, M.; Raman, S.; Wendt, O. F. Chem. Commun. 2015, 51, 911. |
[9] | (g) Moghaddam, F. M.; Tavakoli, G.; Saeednia, B.; Langer, P.; Jafari, B. J. Org. Chem. 2016, 81, 3868. |
[9] | (h) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046. |
[10] | (a) Huang, L.; Li, Q.; Wang, C.; Qi, C. J. Org. Chem. 2013, 78, 3030. |
[10] | (b) Odani, R.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 11045. |
[10] | (c) Huang, L.; Sun, X.; Li, Q.; Qi, C. J. Org. Chem. 2014, 79, 6720. |
[10] | (d) Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2015, 137, 7660. |
[10] | (e) Zhang, X.; Si, W.; Bao, M.; Asao, N.; Yamamoto, Y.; Jin, T. Org. Lett. 2014, 16, 4830. |
[10] | (f) Naksomboon, K.; Valderas, C.; Gómez-Martínez, M.; Álvarez-Casao, Y.; Fernández-Ibáñez, M. Á. ACS Catal. 2017, 7, 6342. |
[11] | (a) Ju, L.; Yao, J.; Wu, Z.; Liu, Z.; Zhang, Y. J. Org. Chem. 2013, 78, 10821. |
[11] | (b) Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842. |
[12] | (a) Pradhan, S.; De, P. B.; Punniyamurthy, T. J. Org. Chem. 2017, 82, 4883. |
[12] | (b) Li, Z.; Su, S.; Qiao, H.; Yang, F.; Zhu, Y.; Kang, J.; Wu, Y.; Wu, Y. Org. Lett. 2016, 18, 4594. |
[12] | (c) Martínez, Á. M.; Rodríguez, N.; Arrayás, R. G.; Carretero, J. C. Chem. Commun. 2014, 50, 2801. |
[13] | (a) Xiong, Y. S.; Zhang, B.; Yu, Y.; Weng, J.; Lu, G. J. Org. Chem. 2019, 84, 13465. |
[13] | (b) Li, J. M.; Wang, Y. H.; Yu, Y.; Wu, R. B.; Weng, J.; Lu, G. ACS Catal. 2017, 7, 2661. |
[14] | (a) Iwasaki, M.; Iyanaga, M.; Tsuchiya, Y.; Nishimura, Y.; Li, W.; Li, Z.; Nishihara, Y. Chem.-Eur. J. 2014, 20, 2459. |
[14] | (b) Iwasaki, M.; Kaneshika, W.; Tsuchiya, Y.; Nakajima, K.; Nishihara, Y. J. Org. Chem. 2014, 79, 11330. |
[15] | Liang, S.; Bolte, M.; Manolikakes, G. Chem.-Eur. J. 2017, 23, 96; |
[16] | Bai, P.; Sun, S.; Li, Z.; Qiao, H.; Su, X.; Yang, F.; Wu, Y.; Wu, Y. J. Org. Chem. 2017, 82, 12119. |
[17] | (a) Rosen, H.; Hajdu, R.; Silver, L.; Kropp, H.; Dorso, K.; Kohler, J.; Sundelof, J. G.; Huber, J.; Hammond, G. G.; Jackson, J. J.; Gill, C. J.; Thompson, R.; Pelak, B. A.; Epstein-Toney, J. H.; Lankas, G.; Wilkening, R. R.; Wildonger, K. J.; Blizzard, T. A.; DiNinno, F. P.; Ratcliffe, R. W.; Heck, J. V.; Kozarich, J. W.; Hammond, M. L. Science 1999, 283, 703. |
[17] | (b) Kamal, A.; Ramakrishna, G.; Nayak, V. L.; Raju, P.; Rao, A. V. S.; Viswanath, A.; Vishnuvardhan, M. V. P. S.; Ramakrishna, S.; Srinivas, G. Bioorg. Med. Chem. 2012, 20, 789. |
[17] | (c) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2013, 57, 2832. |
[18] | (a) Chen, J.; Han, X.; Mei, L.; Liu, J.; Du, K.; Cao, T.; Li, Q. RSC Adv. 2019, 9, 31212. |
[18] | (b) Katrun, P.; Mueangkaew, C.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2014, 79, 1778. |
[19] | (a) da Silva Corre?a, C. M. M.; Waters, W. A. J. Chem. Soc. C 1968, 1874. |
[19] | (b) Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727. |
[19] | (c) Truce, W. E.; Heuring, D. L.; Wolf, G. C. J. Org. Chem. 1974, 39, 238. |
[19] | (d) Liu, L. K.; Chi, Y.; Jen, K.-Y. J. Org. Chem. 1980, 45, 406. |
[19] | (e) Harwood, L. M.; Julia, M.; Thuillier, G. L. Tetrahedron 1980, 36, 2483. |
[19] | (f) Barluenga, J.; Martínez-Gallo, J. M.; Na?jera, C.; Yus, M.; Fananas, F. J. J. Chem. Soc., Perkin Trans. 1 1987, 2605. |
[19] | (g) Na?jera, C.; Baldo?, B.; Yus, M.J. Chem. Soc., Perkin Trans. 1 1988, 1029. |
[19] | (h) daSilva Corre?a, C. M. M.; Fleming, M. D. C. M.; Oliveira, M. A. B. C. S. J. Chem. Soc., erkin Trans. 2 1994, 1993. |
[19] | (i) Na?jera, C.; Sansano, J. M.; Yus, M. J. Chem. Educ. 1995, 72, 664. |
[19] | (j) Craig, D. C.; Edwards, G. L.; Muldoon, C. A. Synlett 1997, 1441. |
/
〈 |
|
〉 |