Recent Advances in Transition Metal-Free Sulfenylation of Indoles

doi:10.6023/cjoc201910020

Abstract

Recently, the direct sulfenylation of C——H bond for C——S formation under transition metal-free conditions has rapidly advanced and is employed for eco-friendly synthesis of sulfenylated natural or bioactive compounds with various sulfenylating reagents. In particular, the sulfenylation of indoles is considered to be the most important because it can lead to a new class of molecules displaying a broad spectrum of biological and pharmaceutical activities. The recent five-year progress in direct C——H bond sulfenylation of indoles under transition metal-free conditions is discussed and their mechanisms in detail are described.

Key words: sulfenylation, indoles, transition metal-free, reaction mechanism, synthetic method

Cite this article

Xu Xinming, Li Jiazhu, Wang Zuli. Recent Advances in Transition Metal-Free Sulfenylation of Indoles[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 886-898.

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References

[1] (a) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
(b) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673.
(c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, 215.
[2] (a) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod. 2000, 63, 596.
(b) Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee, C. O.; Sim, C. J.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2005, 68, 711.
(c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(d) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
[3] Ragno, R.; Coluccia, A.; Regina, G. L.; Martino, G. D.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 3172.
[4] Regina, G. L.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; Martino, G. D.; Matesanz, R.; Díaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.
[5] (a) Berger, J. P.; Doebber, T. W.; Leibowitz, M.; Moller, D. E.; Mosley, R. T.; Tolman, R. L.; Ventre, J.; Zhang, B. B.; Zhou, G. WO 0130343, 2001.
(b) Ramakrishna, V. S. N.; Shirsath, V. S.; Kambhampati, R. S.; Vishwakarma, S.; Kandikere, N. V.; Kota, S.; Jasti, V. WO 2007020653, 2007.
[6] Unangst, P. C.; Connor, D. T.; Stabler, S. R.; Weikert, R. J.; Carethers, M. E.; Kennedy, J. A.; Thueson, D. O.; Chestnut, J. C.; Adolphson, R. L.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360.
[7] (a) Lee, C. F.; Liu, Y. C.; Badsara, S. S. Chem. Asian J. 2014, 9, 706.
(b) Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590.
(c) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
(d) Liu, H.; Jiang, X. Chem. Asian J. 2013, 8, 2546.
(e) Li, G.; Dong, D.; Yu, X.; Wang Z. New J. Chem. 2019, 43, 1667.
(f) Dong, D.; Chen, W.; Yang, Y.; Gao, X.; Wang, Z. ChemistrySelect 2019, 4, 2480.
[8] (a) Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. Chem. Lett. 2020, 31, 49.
(b) Dong, D.-Q.; Hao, S.-H.; Yang, D.-S.; Li, L.-X.; Wang, Z.-L. Eur. J. Org. Chem. 2017, 6576.
(c) Liu, Y.-Y.; Xiong, J.; Wei, L. Chin. J. Org. Chem. 2017, 37, 1667(in Chinese). (刘云云, 熊进, 韦丽, 有机化学, 2017, 37, 1667.)
(d) Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 3338(in Chinese). (徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, 3338.)
(e) Wang, Y.; Liu, Y. Acta Chim. Sinica 2019, 77, 418.
(f) Shamsabadi, A.; Chudasama, V. Org. Biomol. Chem. 2019, 17, 2865.
(g) Guo, Y.; Xiang, Y.; Wei, L.; Wan, J.-P. Org. Lett. 2018, 20, 3971.
(h) Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243.
(i) Reddy Kandimalla, S.; Prathima Parvathaneni, S.; Sabitha, G.; Subba Reddy, B. V. Eur. J. Org. Chem. 2019, 1687.
[9] Nalbandian, C.; Miller, E.; Toenjes, S.; Gustafson, J. L. Chem. Commun. 2017, 53, 1494.
[10] Zou, J.-F.; Huang, W.-S.; Li, L.; Xu, Z.; Zheng, Z.-J.; Yang, K.-F.; Xu, L.-W. RSC Adv. 2015, 5, 30389.
[11] Hostier, T.; Ferey, V.; Ricci, G.; Gomez-Pardo, D.; Cossy, J. Chem. Commun. 2015, 51, 13898.
[12] (a) Freckleton, M.; Baeza, A.; Benavent, L.; Chinchilla, R. Asian J. Org. Chem. 2018, 7, 1006.
(b) Dalpozzo, R. Org. Chem. Front. 2017, 4, 2063.
(c) Liu, Y.-Y.; Zhang, Y.; Hu, C.; Wan, J.; Wen, C. RSC Adv. 2014, 4, 35528.
(d) Zhou, X.; Li, X. RSC Adv. 2014, 4, 1241.
(e) Yang, F.; Tian, S. Angew. Chem., Int. Ed. 2013, 52, 4929.
(f) Katrun, P.; Hongthong, S.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul,V.; Soorukram, D.; Jaipetchb, T.; Kuhakarn, C. RSC Adv. 2014, 4, 18933.
(g) Rao, H.; Wang, P.; Wang, J.; Li, Z.; Sun, X.; Cao, S. RSC Adv. 2014, 4, 49165.
(h) Viglianisi, C.; Marcantoni, E.; Carapacchi, V.; Menichetti, S.; Marsil, L. Eur. J. Org. Chem. 2014, 2014, 6405.
[13] Zhang, H.; Bao, X.; Song, Y.; Qu, J.; Wang, B. Tetrahenron 2015, 71, 8885.
[14] He, Y.-Q.; Liu, S.; Wen, P.; Tian, W.; Ren, X.-Y.; Zhou, Q.; Ma, H.-J.; Huang, G.-S. ChemistrySelect 2016, 1, 1567.
[15] Yi, S.; Li, M.; Mo, W.; Hu, X.; Sun, N.; Jin, L.; Shen, Z. Tetrahedron Lett. 2016, 57, 1912.
[16] Malik, S.; Equbal, D.; Lavekar, A. G.; Sinha, A. K. Org. Biomol. Chem. 2016, 14, 6111.
[17] Choudhury, P.; Roy, B.; Basu, B. Asian J. Org. Chem. 2017, 6, 1569.
[18] Ohkado, R.; Ishikawa, T.; Iida, H. Green Chem. 2018, 20, 984.
[19] Fan, W.; Yang, Z.; Jiang, B.; Li, G. Org. Chem. Front. 2017, 4, 1091.
[20] Bai, F.-C.; Zhang, S.; Wei, L.; Liu, Y.-Y. Asian J. Org. Chem. 2018, 7, 371.
[21] Kong, D.; Huang, T.; Liang, M.; Wu, M.; Lin, Q. Org. Biomol. Chem. 2019, 17, 830.
[22] Guo, W.; Tan, W.; Zhao, M.; Tao, K.; Zheng, L.-Y.; Wu, Y.; Chen, D.; X.-L. RSC Adv. 2017, 7, 37739.
[23] Chen, M.; Luo, Y.; Zhang, C.; Guo, L.; Wang, Q.; Wu, Y. Org. Chem. Front. 2019, 6, 116.
[24] (a) Chen, S.-Q.; Wang, Q.-M.; Xu, P.-C.; Ge, S.-P.; Zhong, P.; Zhang, X.-H. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 100.
(b) Rahaman, R.; Devi, N.; Barman, P. Tetrahedron Lett. 2015, 56, 4224.
(c) Devi, N.; Rahaman, R.; Sarma, K.; Khan, T.; Barman, P. Eur. J. Org. Chem. 2017, 2017, 1520.
(d) Rafique, J.; Saba, S.; Rosrio, A. R.; Braga, A. L. Chem.-Eur. J. 2016, 22, 11854.
(e) Bettanin, L.; Saba, S.; Doerner, C. V.; Franco, M. S.; Godoi, M.; Rafique, J.; Braga, A. L. Tetrahedron 2018, 74, 3971.
[25] Thurow, S.; Penteado, F.; Perin, G.; Alves, D.; Santi, C.; Monti, B.; Schiesser, C. H.; Lenardao, E. J. Org. Chem. Front. 2018, 5, 1983.
[26] Ye, L.-M.; Chen, J.; Mao, P.; Zhang, X.-J.; Yan, M. Tetrahedron Lett. 2017, 58, 2743.
[27] Yu, Y.; Zhou, Y.; Song, Z.-Q.; Liang, G. Org. Biomol. Chem. 2018, 16, 4958.
[28] Liu, C.; Ding, L. Org. Biomol. Chem. 2015, 13, 2251.
[29] Rahaman, R.; Devi, N.; Bhagawati, J. R.; Barman, P. RSC Adv. 2016, 6, 18929.
[30] Al-Saedy, M. A. E.; Joseph, A.-C. M. A. N.; Harrity, P. A. Synlett 2017, 28, 349.
[31] Liu, C.; Fan, J.; Wu, M.; Chen, J.-H.; Zhao, Y.; Xie, M.-H. Chin. J. Chem. 2018, 36, 819.
[32] Zhao, X.; Wei, A.; Yang, B.; Li, T.-J.; Li, Q.; Qiu, D.; Lu, K. J. Org. Chem. 2017, 82, 9175.
[33] Zhao, X.; Zheng, X.; Tian, M.-M.; Sheng, J.; Tong, Y.-F.; Lu, K. Tetrahedron 2017, 73, 7233.
[34] Yang, X.; Bao, Y.; Dai, Z.; Zhou, Q.; Yang, F. Green Chem. 2018, 20, 3727.
[35] Siauciulis, M.; Sapmaz, S.; Pulis, A. P.; Procter, D. J. Chem. Sci. 2018, 9, 754.
[36] (a) Gullapalli, K.; Ragam, R.; Narayanarao, V. RSC Adv. 2015, 5, 22718.
(b) Lu, K.; Deng, Z.; Li, M.; Li, T.; Zhao, X. Org. Biomol. Chem. 2017, 15, 1254.
(c) Zhao, X.; Wei, A.; Li, T.; Su, Z.; Chen, J.; Lu, K. Org. Chem. Front. 2017, 4, 232.
[37] He, Y.; Jiang, J.; Bao, W.; Deng, W.; Xiang, J. Tetrahedron Lett. 2017, 58, 4583.
[38] Equbal, D.; Saima, R. S.; Lavekar, A. G.; Sinha, A. K. J. Org. Chem. 2019, 84, 2660.
[39] Ghosh, A.; Lecomte, M.; Kim-Lee, S.-H.; Radosevich, A. T. Angew. Chem., Int. Ed. 2019, 58, 2864.
[40] Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560.
[41] Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.; Zha, Z.; Wang, Z. Green Chem. 2016, 18, 2609.
[42] Rahaman, R.; Devi, N.; Sarma, K.; Barman, P. RSC Adv. 2016, 6, 10873.
[43] (a) Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066.
(b) Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125.
(c) Xiao, F. H.; Xie, H.; Liu, S. W.; Deng, G. J. Adv. Synth. Catal. 2014, 356, 364.
[44] Qi, H.; Zhang, T.; Wan, K.-F.; Luo, M.-M. J. Org. Chem. 2016, 81, 4262.
[45] Li, J.; Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Biomol. Chem. 2016, 14, 9384.
[46] Rahaman, R.; Barman, P. Eur. J. Org. Chem. 2017, 2017, 6327.

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