Research Progress on Cross-Coupling with Aryl Sulfonyl andSulfinate Compounds

doi:10.6023/cjoc201504042

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2259-2274.DOI: 10.6023/cjoc201504042 Previous Articles Next Articles

Reviews

芳基磺酰和亚磺酸类化合物参与的偶联反应研究进展

张诗浓^a,b, 杨胜虎^a, 黄乐浩^a, 赵保丽^a, 程凯^a, 齐陈泽^a

a 绍兴文理学院浙江省精细化学品传统工艺替代技术研究重点实验室绍兴 312000;
b 绍兴市质量技术监督检测院绍兴 312000

收稿日期:2015-04-27 修回日期:2015-06-19 发布日期:2015-07-08
通讯作者: 程凯 E-mail:chengkai@usx.edu.cn
基金资助:
国家自然科学基金(No. 21402123)、浙江省自然科学基金(Nos. LQ14B020001, LQ14B020001)、浙江省大学生科技创新活动计划(No. 2014R426012)、浙江省教育厅(No. Y201328443)和绍兴市科技计划(No. 2013B70018)资助项目.

Research Progress on Cross-Coupling with Aryl Sulfonyl andSulfinate Compounds

Zhang Shinong^a,b, Yang Shenghu^a, Huang Lehao^a, Zhao Baoli^a, Cheng Kai^a, Qi Chenze^a

a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000;
b Shaoxing Testing institute of Quality Technical Supervision, Shaoxing 312000

Received:2015-04-27 Revised:2015-06-19 Published:2015-07-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21402123), the Zhejiang Provincial Natural Science Foundation (Nos. LQ14B020001, LQ13B020001), the Undergraduate Science Technology Innovation of Zhejiang Province (No. 2014R426012), the Education Department of Zhejiang Province (No. Y201328443) and the Foundation of Science and Technology Bureau of Shaoxing (No. 2013B70018).

Cross-coupling reactions of aryl sulfonyl and sulfinate compounds have been well developed as an efficient synthetic method in recent years. Aryl sulfonyl chlorides, arylsulfinates and arylsulfonyl hydrazides have been used as desulfitative arylation, arylsulfonylation and reductive aryl sulfidation reagents in the synthesis of biaryls, aryl sulfones and aryl sulfides. The research progress on cross-coupling with aryl sulfonyl and sulfinate compounds combined with our work is reviewed, focusing on applications and progress in new synthetic method to construct carbon-carbon, carbon-sulfonyl and carbon-sulfur bond.

Key words: aryl sulfonyl compounds, arylsulfinate compounds, cross-coupling, arylation, arylsulfonylation, aryl sulfidation

Cite this article

Zhang Shinong, Yang Shenghu, Huang Lehao, Zhao Baoli, Cheng Kai, Qi Chenze. Research Progress on Cross-Coupling with Aryl Sulfonyl andSulfinate Compounds[J]. Chin. J. Org. Chem., 2015, 35(11): 2259-2274.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014, 12, 9743.
[2] Vogel, P.; Dubbaka, S. R. Org. Lett. 2004, 6, 95.
[3] Vogel, P.; Dubbaka, S. R. J. Am. Chem. Soc. 2003, 125, 15292.
[4] Dubbaka, S. R.; Vogel, P. Adv. Synth. Catal. 2004, 346, 1793
[5] Vogel, P.; Dubbaka, S. R. Chem. Eur. J. 2005, 11, 2633.
[6] Vogel, P.; Dubbaka, S. R. Tetrahedron Lett. 2006, 47, 3345.
[7] Kashiwabara, T.; Tanaka, M. Tetrahedron Lett. 2005, 46, 7125.
[8] Luo, M.; Zhang, S.; Zeng, X.; Wei, Z.; Zhao, D.; Kang, T.; Zhang, W.; Yan, M. Synlett 2006, 1891.
[9] Zhang, W.; Liu, F.; Li, K.; Zhao, B. Appl. Organomet. Chem. 2014, 28, 379.
[10] Zhao, X.; Dimitrijevi?e, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466.
[11] Cheng, J.; Zhang, M.; Zhang, S.; Liu, M. Chem. Commun. 2011, 47, 11522.
[12] Yuan, K.; Doucet, H. Chem. Sci. 2014, 5, 392.
[13] Zhang, W.; Liu, F.; Zhao, B. Appl. Organomet. Chem. 2015, 29, 524.
[14] Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Org. Lett. 2004, 6, 2105.
[15] Deng, G. S.; Sun, T.; Zhou, J.; Chin. J. Org. Chem. 2012, 32, 1872 (in Chinese). (邓桂胜, 孙腾飞, 周佳, 有机化学, 2012, 32, 1872.)
[16] Zhao, X.; Dong, V. M. Angew. Chem., Int. Ed. 2011, 50, 932.
[17] Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298.
[18] Wu, A.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
[19] Ge, B.; Wang, D.; Dong, W. Tetrahedron Lett. 2014, 55, 5443.
[20] Wang, D.; Ge, B.; Yu, X.; Miao, H.; Ding, Y. Chin. J. Org. Chem. 2015, 35, 676 (in Chinese). (王大伟, 葛冰洋, 余晓丽, 苗红艳, 丁玉强, 有机化学, 2015, 35, 676.)
[21] Wu, Q.; Zhao, D. B.; Qin, X. R.; Lan, J. B.; You, J. S. Chem. Commun. 2011, 47, 9188.
[22] Chen, M.; Huang, Z. T.; Zheng, Q. Y. Chem. Commun. 2012, 48, 11686.
[23] Deng, G. J.; Zhou, X.; Luo, J.; Liu, J.; Peng, S. Org. Lett. 2011. 13, 1432.
[24] Liu, S.; Bai, Y.; Cao, X.; Xiao, F.; Deng, G. J. Chem. Commun. 2013, 49, 7501.
[25] Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2014, 356, 2029.
[26] Forgione, P.; Ortgies, D. H.; Barthelme, A.; Aly, S.; Desharnais, B.; Rioux, S. Synthesis 2013, 45, 694.
[27] Cheng, K.; Hu, S.; Zhao, B.; Zhang, X.-M. Qi, C. J. Org. Chem. 2013, 78, 5022.
[28] Cheng, K.; Yu, H.-Z.; Zhao, B.; Hu, S.; Zhang, X.-M.; Qi, C. RSC Adv. 2014, 4, 57923.
[29] Luo, M.; Rao, B.; Zhang, W.; Hu, L. Green Chem. 2012, 14, 3436.
[30] Li, C. J.; Rao, H.; Yang, L.; Shuai, Q. Adv. Synth. Catal. 2011, 353, 1701.
[31] Deng, G. J.; Li. C. J.; Liu, J.; Zhou, X.; Rao, H.; Xiao, F. Chem. Eur. J. 2011, 17, 7996.
[32] Behrends, M.; Sävmarker, J.; Sjöberg, P. J. R.; Larhed, M. ACS Catal. 2011, 1, 1455.
[33] You, J.; Liu, B.; Guo, Q.; Cheng, Y.; Lan, J. Chem. Eur. J. 2011, 17, 13415.
[34] Deng, G. J.; Chen, R.; Liu, S.; Liu, X.; Luo, Y. Org. Biomol. Chem. 2011, 9, 7675.
[35] Wang, L.; Wang, M.; Li, D.; Zhou, W. Tetrahedron 2012, 68, 1926.
[36] Deng, G. J.; Luo, H. A.; Wu, M.; Luo, J.; Xiao, F.; Zhang, S. Adv. Synth. Catal. 2012, 354, 335.
[37] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M. Synlett 2003, 361.
[38] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M.; Bernini, R. J. Org. Chem. 2004, 69, 5608.
[39] Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239.
[40] Wang, Z.; Baskin, J. M. Org. Lett. 2002, 4, 4423.
[41] Ma, D.; Zhu, W. J. Org. Chem. 2005, 70, 2696.
[42] Guo, S.; Yuan, Y. Synlett 2011, 2750.
[43] Beaulieu, C.; Guay, D.; Wang, Z.; Evan, D. A. Tetrahedron Lett. 2004, 45, 3233.
[44] Batey, R. A.; Huang, F. Tetrahedron 2007, 63, 7667.
[45] Tse, M. K.; Kar, A.; Sayyed, I. A.; Lo, W. F.; Kaiser, H. M.; Beller, M. Org. Lett. 2007, 9, 3405.
[46] Kantam, M. L.; Neelima, B.; Sreedhar, B.; Chakravarti, R. Synlett 2008, 1455.
[47] Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chem. Eur. J. 2011, 17, 5652.
[48] Zhang, W.; Li, K.; Zhao, B. J. Chem. Res. 2014, 38, 269.
[49] Kuwano, R.; Kondo, Y.; Shirahama, T. Org. Lett. 2005, 7, 2973.
[50] Sreedhar, B.; Reddy, M. A.; Reddy, P. S. Adv. Synth. Catal. 2010, 352, 1861.
[51] Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 188.
[52] Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2014, 356, 2029.
[53] Xiao, F. H.; Xie, H.; Liu, S. W.; Deng, G. J. Adv. Synth. Catal. 2014, 356, 364.
[54] Yang, F. L.; Ma, X. T.; Tian, S. K. Chem. Eur. J. 2012, 18, 1582.
[55] Chen, W.; Chen, H.; Xiao, F.; Deng, G. J. Org. Biomol. Chem. 2013, 11, 4295.
[56] You, J.; Liu, B.; Li, J.; Song, F. Chem. Eur. J. 2012, 18, 10830.
[57] Yu, X.; Li, X.; Wan, B. Org. Biomol. Chem. 2012, 10, 7479.
[58] Kwong, F. Y.; Yuen, O. Y.; So, C. M.; Wong, W. T. Synlett 2012, 2714.
[59] Wu, X.-M.; Wang, Y. Synlett 2014, 25, 1163.
[60] Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem. Eur. J. 2014, 20, 7911.
[61] Tang, S.; Wu, Y.; Liao, W.; Bai, R.; Liu, C.; Lei, A. Chem. Commun. 2014, 50, 4496.
[62] Wang, H.; Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, J.; Suo, Y. Chem. Commun. 2013, 49, 10239.
[63] Yang, Y.; Tang, L.; Zhang, S.; Guo, X.; Zha, Z.; Wang, Z. Green Chem. 2014, 16, 4106.
[64] Li, X.; Shi, X.; Fang, M.; Xu, X. J. Org. Chem. 2013, 78, 9499.
[65] Wang, J.; Xu, C.; Wei, S.; Zhao, B.; Cheng, K. Chin. J. Org. Chem. 2014, 34, 767 (in Chinese).(王建伟, 徐程见, 韦珊红, 赵保丽, 程凯, 有机化学, 2014, 34, 767.)
[66] Singh, N.; Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 5874.
[67] Singh, R.; Allam, B. K.; Singh, N.; Kumari, K.; Singh, S. K.; Singh, K. N. Adv. Synth. Catal. 2015, 357, 1181.
[68] Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 4202.
[69] Yang, F. L.; Wang, F. X.; Wang, T. T.; Wang, Y. J.; Tian, S. K. Chem. Commun. 2014, 50, 2111.
[70] Guo, S.; He, W.; Xiang, J.; Yuan, Y. Chem. Commun. 2014, 50, 8578.
[71] Zhao, X.; Zhang, L.; Li, T.; Liu, G.; Wang, H.; Lu, K. Chem. Commun. 2014, 50, 13121.
[72] Yan, R.; Kang, X.; Yan, R.; Yu, G.; Pang, X.; Liu, X.; Li, X.; Xiang, L.; Huang. G. J. Org. Chem. 2014, 79, 10605.
[73] Tian, S. K.; Yang, F. L. Angew. Chem., Int. Ed. 2013, 52, 4929.
[74] Wang, G. W.; Miao, T. Chem. Eur. J. 2011, 17, 5787.
[75] Wang, G. W.; Miao, T. Chem. Commun., 2011, 47, 9501.
[76] Duan, C.; Li, Y.; Wang, H.; Zhang, R.; Jin, K.; Zhao, D. J. Org. Chem. 2012, 77, 4849.
[77] Liu, C.-R.; Ding, L.-H. Org. Biomol. Chem. 2015, 13, 2251.

芳基磺酰和亚磺酸类化合物参与的偶联反应研究进展

Research Progress on Cross-Coupling with Aryl Sulfonyl andSulfinate Compounds

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200) [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.
[2]	Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.
[3]	Yuxing Tong, Ziwei Wang, Ben Liu, Yaowei Xu, Song Gao, Xiangbing Tang, Xinghua Zhang. Recent Advances in Synthesis of 3-Sulfenylated Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1310-1324.
[4]	Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.
[5]	Dongping Chen, Chunhong Yang, Ming Li, Guoxiao Zhao, Wenpeng Wang, Xicun Wang, Zhengjun Quan. Recent Progress on Arylation with Aryne through Three-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 503-525.
[6]	Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470.
[7]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[8]	Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.
[9]	Xuefeng Jia, Xiangjuan Tong. Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2640-2658.
[10]	Xiaojie Liu, Biping Xu, Weiping Su. Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2184-2191.
[11]	Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.
[12]	Xue Li, Cong Wang, Tiezheng Jia. Recent Advances in N-Arylation of NH-Sulfoximines and Their Applications [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 714-731.
[13]	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.
[14]	Siqi Cong, Mengya Liu, Siyuan Peng, Qiucui Zheng, Mengjiao Li, Yan Guo, Feixian Luo. Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 384-390.
[15]	Gaoxu Han, Hongtao Xu, Wei Hou. Rhodium(III) Catalyzed C(sp³)—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 391-423.