Iodine Catalyzed Thiolation of Electron Rich Compounds with Benzenesulfonyl Chlorides

doi:10.6023/cjoc201604056

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (11): 2757-2762.DOI: 10.6023/cjoc201604056 Previous Articles Next Articles

Notes

碘催化芳基磺酰氯与富电子化合物的硫醚化反应

王丁意, 张荣兴, 林森, 邓瑞红, 严兆华

南昌大学化学学院南昌 330031

收稿日期:2016-04-26 修回日期:2016-06-25 发布日期:2016-07-08
通讯作者: 林森 E-mail:senlin@ncu.edu.cn
基金资助:
国家自然科学基金（No.21362022）资助项目.

Iodine Catalyzed Thiolation of Electron Rich Compounds with Benzenesulfonyl Chlorides

Wang Dingyi, Zhang Rongxing, Lin Sen, Deng Ruihong, Yan Zhaohua

College of Chemistry, Nanchang University, Nanchang 330031

Received:2016-04-26 Revised:2016-06-25 Published:2016-07-08
Supported by:
Project supported by the National Natural Science Foundation of China (No.21362022).

1. Iodine Catalyzed Thiolation of Electron Rich Compounds with Benzenesulfonyl Chlorides.PDF(1335KB)

Abstract

Cite this article

Wang Dingyi, Zhang Rongxing, Lin Sen, Deng Ruihong, Yan Zhaohua. Iodine Catalyzed Thiolation of Electron Rich Compounds with Benzenesulfonyl Chlorides[J]. Chin. J. Org. Chem., 2016, 36(11): 2757-2762.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. A.; Liu, X. Chem. Soc. Rev. 2015, 44, 291.
(b) Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379.
(c) Guo, X.-X.; Gu, D.-W.; Wu, Z.; Zhang, W. Chem. Rev. 2014, 115, 1622.
(d) Noisier, A. F.; Brimble, M. A. Chem. Rev. 2014, 114, 8775.
(e) Abdoli, M.; Mirjafary, Z.; Saeidian, H.; Kakanejadifard, A. RSC Adv. 2015, 5, 44371.
(f) Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, 1155.
(g) Huang, Z.; Lim, H. N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764.
(h) Yang, J. Org. Biomol. Chem. 2015, 13, 1930.
(i) Zhang, Y.; Feng, B. Chin. J. Org. Chem. 2014, 34, 2406 (in Chinese). (张艳, 冯柏年, 有机化学, 2014, 34, 2406.)
(j) Shan, X. J.; Liu, Z. Q. Chin. J. Org. Chem., 2015, 35, 522 (in Chinese). (尚筱洁, 柳忠全, 有机化学, 2015, 35, 522.)
(k) Gang, F. L.; Xu, G. L.; Dong, T. S.; Yang, L.; Du, Z. Y. Chin. J. Org. Chem. 2015, 35, 1428 (in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
(l) S. X. J.; L. Z. Q. Acta Chim. Sinica 2015, 73, 1275 (in Chi-nese). (尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)
(m) Yu, J. Q.; Ding, K. L. Acta Chim. Sinica 2015, 73, 1223 (in Chinese). (余金权, 丁奎岭, 化学学报, 2015, 73, 1223.)
(n) Zong, C.; Liu, J.; Chen, S.; Zeng, R.; Zou, J. Chin. J. Chem. 2014, 32, 212.
[2] (a) Nakazawa, T.; J. Xu.; Nishikawa, T.; Oda, T.; Fujita, A.; Ukai, K.; Mangindaan, R. E. P.; Rotinsulu, H.; Kobayashi, H.; Namikoshi, M. J. Nat. Prod. 2007, 70, 439.
(b) Gingras, M.; Chabre, Y. M.; Roy, M.; Roy, R. Chem. Soc. Rev. 2013, 42, 4823.
(c) Takimiya, K.; Shinamura, S.; Osaka, I.; Miyazaki, E. Adv. Mater. 2011, 23, 4347.
(d) Sizov, A. Y.; Kovergin, A. N.; Ermolov, A. F. Russ. Chem. Rev. 2003, 72, 357.
(e) Mori, T.; Nishimura, T.; Yamamoto, T.; Doi, I.; Miyazaki, E.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2013, 135, 13900.
(f) Oda, T.; Fujiwara, T.; Liu, H.; Ukai, K.; Mangindaan, R. E. P.; Mochizuki, M.; Namikoshi, M. Marine Drugs 2006, 4, 15.
[3] (a) Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
(b) Sperotto, E.; van Klink, G. P.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625.
(c) Zhang, Y.; Ngeow, K. C.; Ying, J. Y. Org. Lett. 2007, 9, 3495.
(d) Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189.
(e) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
(f) Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613.
(f) Wan, J.-P.; Zhong, S.; Xie, L.; Cao, X.; Liu, Y.; Wei, L. Org. Lett. 2016, 18, 584.
(g) Liu, Y.; Zhang, Y.; Hu, C.; Wan, J.-P.; Wen, C. RSC Adv. 2014, 4, 35528.
(h) Liu, Y.; Wang, H.; Zhang,J.; Wan, J.-P.; Wen, C. RSC Adv.,2014, 4, 19472.
[4] (a) Zou, L.-H.; Reball, J.; Mottweiler, J.; Bolm, C. Chem. Commun. 2012, 48, 11307.
(b) Katrun, P.; Hongthong, S.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn, C. RSC Adv. 2014, 4, 18933.
(c) Kang, X.; Yan, R.; Yu, G..; Pang, X.; Liu, X.; Li, X.; Xiang, L.; Huang, G. J. Org. Chem. 2014, 79, 10605.
(d) Lin, Y.-M.; Lu, G.-P.; Cai, C.; Yi, W.-B. Org. Lett. 2015, 17, 3310.
(e) Hiebel, M.-A.; Berteina-Raboin, S. Green Chem. 2015, 17, 937.
(f) Yang, F. L.; Tian, S. K. Angew. Chem., Int. Edit. 2013, 125, 5029.
(g) Zhao, X.; Zhang, L.; Lu, X.; Li, T.; Lu, K. J. Org. Chem. 2015, 80, 2918.
(h) D., Y.-C.; Wei. W.; Huang, Y.; Zhou, A. Org. Biomol. Chem. 2016, 14, 1428.
[5] (a) Wu, Q.; Zhao, D.; Qin, X.; Lan, J.; You, J. Chem. Commun. 2011, 47, 9188.
(b) Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun, 2012, 48, 11686.
[6] (a) Nakazawa, T.; Xu. J.; Nishikawa, T.; Oda, T.; Fujita, A.; Ukai,K.; Mangindaan, R. E. P.; Rotinsulu, H.; Kobayashi, H.; Namikoshi, M. J. Nat. Prod. 2007, 70, 439.
(b) Gingras, M.; Chabre, Y. M.; Roy, M.; Roy, R. Chem. Soc. Rev. 2013, 42, 4823.
(c) Takimiya, K.; Shinamura, S.; Osaka, I.; Miyazaki, E. Adv. Mater. 2011, 23, 4347.
(d) Sizov, A. Y.; Kovergin, A. N.; Ermolov, A. F. Russ. Chem. Rev. 2003, 72, 357.
(e) Okubo, T.; Yoshikawa, R.; Chaki, S.; Okuyama, S.; Nakazato, A. Bioorg. Med. Chem. 2004, 12, 423.
(f) Ueda, T.; Mizusgige, K.; Yukiiri, K.; Takahashi, T. Cerebro-vasc. Dis. 2003, 16, 396.
(g) Ferlin, M. G.; Chiarelotto, G.; Acqua, S. D.; Maciocco, E.; Mascia, M. P.; Pisuand, M. G.; Biggio, G. Bioorg. Med. Chem. 2005, 13, 3531.
(h) Chande, M. S.; Barve, P. A.; Suryanarayan, V. J. Heterocycl. Chem. 2007, 44, 49.
(i) Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. J. Med. Chem. 2007, 50, 5053.
(j) Caruso, F.; Pettinari, C.; Marchetti, F.; Natanti, P.; Phillips, C., Tanski, J.; Rossi, M. Inorg. Chem. 2007, 46, 7553.
[7] (a) Chen, Y.; Xiao, F.; Chen, H.; Liu, S.; Deng, G.-J. RSC Adv. 2014, 4, 44621.
(b) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292.
(c) Harwood, L.; Julia, M. Tetrahedron 1981, 12, 2483.
[8] Parumala, S. K. R.; Peddinti, R. K. Green Chem. 2015, 17, 4068.
[9] Huang, X.; Wang, S.; Li, B.; Wang, X.; Ge, Z., Li, R. RSC Adv. 2015, 5, 22654.
[10] Zhao, X.; Zhang, L.; Li, T.; Liu, G.; Wang, H.; Lu, K. Chem. Commun. 2014, 50, 13121.
[11] Takizawa, S.-Y.; Nishida, J.-I.; Tsuzuki, T.; Tokito. S.; Yamashita, Y. Inorg. Chem. 2007, 46, 4308.
[12] Ge, W.; Zhu, X.; Wei, Y. Eur. J. Org. Chem. 2013, 2013, 6015.
[13] Purohit, V. B.; Karad, S. C.; Patel, K. H.; Raval, D. K. Tetrahedron 2016, 72, 1114.

[1]	Tongyang Cao, Wei Li, Lijing Wang. Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 508-524.
[2]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[3]	Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.
[4]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[5]	Yu Zhao, Yurong Duan, Shihui Shi, Yubin Bai, Liangzhu Huang, Xiaojun Yang, Yantu Zhang, Bin Feng, Jianbo Zhang, Qiuyu Zhang. Recent Advances of Hypervalent Iodine(III) Reagents upon Visible Light Irradiation [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4106-4140.
[6]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[7]	Haojie Ma, Fengyuan Zhou, Fanwen Su, Bo Han, Ran Li, Yuqi Zhang, Jijiang Wang. Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3960-3965.
[8]	Qianmin Li, Manman Wang, Wenquan Yu, Junbiao Chang. Synthesis of β-Nitroamines and α-Aminonitriles by I₂-Mediated Oxidative C—C Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3966-3976.
[9]	Yun Shi, Ting Xiao, Dong Xia, Wenchao Yang. SCF₃ Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2715-2727.
[10]	Xiaoxiao Yu, Wangheng Bai, Jianye Zhu, Yuting Zhang, Mengru Zhang, Jiwei Wu. Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2449-2455.
[11]	Meng Li, Kai Sun. Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F₃CS-Containing Quinolinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2089-2097.
[12]	Bing Liu, Zhichuang Wang, Kai Sun, Shi Tang, Xin Wang. Silver-Mediated Radical Trifluoromethylthiolation Cyclization: Synthesis of CF₃S-Containing Benzimidazole[2,1-a]isoquinolines [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1387-1395.
[13]	Jiajia Lu, Junli Yang, Jie Gu, Ju Yang, Zhenjie Gao, Lijiao Su, Xin Tao, Mingwei Yuan, Lijuan Yang. Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^– [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1474-1482.
[14]	Fufang Wu, Xuejian Li, Hao Jia, Xuanzhen Han, Xiaobao Shen. Iodine(III)-Promoted Oxidative Cross-Coupling Reactions of C—H Bonds via a Free Radical Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 884-890.
[15]	Ruiqin Zhang, Renchao Ma, Qinjiao Fu, Jing Chen, Yongmin Ma. I₂/PhNO₂ Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 854-862.

碘催化芳基磺酰氯与富电子化合物的硫醚化反应

Iodine Catalyzed Thiolation of Electron Rich Compounds with Benzenesulfonyl Chlorides

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments