Recent Advances in Cyclization Reaction of Alkynes under Transition Metal-Free Conditions

doi:10.6023/cjoc201912029

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1529-1539.DOI: 10.6023/cjoc201912029 Previous Articles Next Articles

无过渡金属参与的炔烃环化反应研究进展

张磊^a, 袁斯甜^b, 王鹏^c, 刘晋彪^d

a 中南大学冶金与环境学院长沙 410083;
b 南昌海关技术中心南昌 330002;
c 嘉兴学院生物与化学工程学院浙江嘉兴 314001;
d 江西理工大学冶金与化学工程学院江西赣州 341000

收稿日期:2019-12-21 修回日期:2020-01-24 发布日期:2020-03-04
通讯作者: 王鹏, 刘晋彪 E-mail:liujinbiao@jxust.edu.cn;815207636@qq.com
基金资助:
国家自然科学基金（Nos.21762018，21961014）、湖南省研究生创新（No.CX20190060）、中南大学中央高校基础研究基金及江西理工大学大学生创新创业训练计划（No.201910407015）资助项目.

Recent Advances in Cyclization Reaction of Alkynes under Transition Metal-Free Conditions

Zhang Lei^a, Yuan Sitian^b, Wang Peng^c, Liu Jinbiao^d

a School of Metallurgy and Environment, Central South University, Changsha 410083;
b Technology Center of Nanchang Customs, Nanchang 330002;
c College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001;
d School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000

Received:2019-12-21 Revised:2020-01-24 Published:2020-03-04
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21762018, 21961014), the Hunan Provincial Innovation Foundation for Postgraduate (No. CX20190060), the Fundamental Research Funds for the Central Universities of Central South University, and the Innovation and Entrepreneurship Training Program of Jiangxi University of Science and Technology (No. 201910407015).

Remarkable achievements have been made in the construction of carbocyclic (heterocyclic) compounds through cyclization reaction of alkynes. It is vitally important to achieve the high selectivity of cyclization reactions, and neighboring group-participated selective cyclization reaction of alkynes is widely considered as an effective strategy. In this review, the recent advances in neighboring group-participated cyclization reaction of alkynes under transition metal-free conditions are summarized.

Key words: alkynes, neighboring group, transition metal-free, cyclization reaction

Cite this article

Zhang Lei, Yuan Sitian, Wang Peng, Liu Jinbiao. Recent Advances in Cyclization Reaction of Alkynes under Transition Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1529-1539.

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[1] (a) Boyarskiy, V. P.; Ryabukhin, D. S.; Bokach, N. A.; Vasilyev, A. V. Chem. Rev. 2016, 116, 5894.
(b) Zheng, Z. T.; Wang, Z. X.; Wang, Y. L.; Zhang, L. M. Chem. Soc. Rev. 2016, 45, 4448.
(c) Yuan, S. T.; Zhou, H. W.; Gao, L.; Liu, J. B.; Qiu, G. Y. S. Org. Lett. 2018, 20, 562.
(d) Wang, Y. C.; Wang, R. X.; Qiu, G. Y. S.; Zhou, H. W.; Xie, W. L.; Liu, J. B. Org. Chem. Front. 2019, 6, 2471.
[2] (a) Huang, S. Y.; Li, X. X.; Lin, C. L.; Tang, W. P. Chem. Commun. 2012, 48, 2204.
(b) Chen, D. P.; Xing, G. D.; Zhou, H. W. Org. Chem. Front. 2015, 2, 947.
(c) Zhou, P.; Qiu, H. H.; Shi, J. C. Chin. J. Org. Chem. 2016, 36, 425(in Chinese). (周鹏, 邱会华, 施继成, 有机化学, 2016, 36, 425.)
(d) Yu, J. J.; Yang, S.; Wu, Z.; Zhu, C. Chin. J. Org. Chem. 2019, 39, 223(in Chinese). (余佳佳, 杨珊, 吴镇, 朱晨, 有机化学, 2019, 39, 223.)
(e) Mei, H. B.; Yin, Z. Z.; Liu, J.; Sun, H. L.; Han, J. L. Chin. J. Chem. 2019, 37, 292.
[3] (a) Kirsch, S. F. Synthesis 2008, 3183.
(b) Jung, H. H.; Floreancig, P. E. J. Org. Chem. 2007, 72, 7359.
(c) Zhang, J.; Xiao, G. M. Petrochem. Technol. 2011, 40, 579(in Chinese). (张进, 肖国民, 石油化工, 2011, 40, 579.)
(d) Wang, Y.-C.; Wang, R.-X.; Qiu, G.; Zhou, H.; Xie, W.; Liu, J.-B. Org. Chem. Front. 2019, 6, 2471.
(e) Wang, Y. D.; Li, J. H.; Gao, Y.; Yang, Y.; Gao, Y.; Xu, Z. F. Hydrometallurgy 2020, 191, 105220.
(f) Wang, Y. C.; Liu, J. B.; Zhou, H. W.; Xie, W. L.; Rojsitthisak, P.; Qiu, G. Y. S. J. Org. Chem. 2020, 85, 1906.
[4] (a) Wang, Z.; Yang, L.; Liu, H. L.; Tan, Y. Z.; Bao, W. H.; Wang, M.; Tang, Z. W.; He, W. M. Chin. J. Org. Chem. 2018, 38, 2639(in Chinese). (王峥, 杨柳, 刘慧兰, 谭英芝, 包文虎, 汪明, 唐子龙, 何卫民, 有机化学, 2018, 38, 2639.)
(b) Lu, L. H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2019, 30, 1237.
(c) Cao, Z.; Zhu, Q.; Lin, Y. W.; He, W. M. Chin. Chem. Lett. 2019, 30, 2132.
(d) Wu, C.; Wang, Z.; Hu, Z.; Zeng, F.; Zhang, X. Y.; Cao, Z.; Tang, Z.; He, W. M. Org. Biomol. Chem. 2018, 16, 3177.
(e) Wu, C.; Xiao, H. J.; Wang, S. W.; Tang, Z. L.; Xia, W.; Li, W. F.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 2169.
(f) Yuan, S.; Wang, Y.; Qiu, G.; Liu, J.-B. Chin. J. Org. Chem. 2017, 37, 566(in Chinese). (袁斯甜, 王艳华, 邱观音生, 刘晋彪, 有机化学, 2017, 37, 566.)
[5] (a) Wen, B.; Petersen, J. L.; Wang, K. K. Org. Lett. 2010, 13, 168.
(b) Zhu, H. T.; Ji, K. D.; Yang, F.; Wang, L. J.; Zhao, S. C.; Ali, S.; Liu, X. Y.; Liang, Y. M. Org. Lett. 2011, 13, 684.
(c) Yang, X. B.; Hu, F. Z.; Di, H. J.; Cheng, X. X.; Li, D.; Kan, X. L.; Zou, X. M.; Zhang, Q. C. Org. Biomol. Chem. 2014, 12, 8947.
(d) Luo, P. S.; Tang, R. Y.; Zhong, P.; Li, J. H. Chin. J. Org. Chem. 2009, 29, 1924(in Chinese). (罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.)
[6] Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.
[7] Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
[8] Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 7301.
[9] Stoll, A. H.; Knochel, P. Org. Lett. 2008, 10, 113.
[10] Arcadi, A.; Bianchi, G.; Inesi, A.; Marinelli, F.; Rossi, L. Eur. J. Org. Chem. 2008, 2008, 783.
[11] (a)Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
(b)Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62.
[12] Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem.-Eur. J. 2010, 16, 3005.
[13] Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Kuhakarn, C. Org. Biomol. Chem. 2017, 15, 3662.
[14] Han, D. D.; Li, Z. M.; Fan, R. H. Org. Lett. 2014, 16, 6508.
[15] Shi, Q.; Li, P. H.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322.
[16] Chen, F.; Meng, Q.; Han, S. Q.; Han, B. Org. Lett. 2016, 18, 3330.
[17] Zhou, N. N.; Yan, Z. F.; Zhang, H. L.; Wu, Z. K.; Zhu, C. J. Org. Chem. 2016, 81, 12181.
[18] Huo, Z. B.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2010, 75, 1266.
[19] (a) Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 4764.
(b) Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z. B. Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720.
[20] Bianchi, G.; Chiarini, M.; Marinelli, F.; Rossi, L.; Arcadi, A. Adv. Synth. Catal. 2010, 352, 136.
[21] Kanazawa, C.; Terada, M. Chem.-Asian J. 2009, 4, 1668.
[22] Dev, K.; Maurya, R. RSC Adv. 2015, 5, 13102.
[23] Brahmchari, D.; Verma, A. K.; Mehta, S. J. Org. Chem. 2018, 83, 3339.
[24] Tan, J.; Tong, Y.; Chen, Z. Y. ChemistrySelect 2018, 3, 3886.
[25] Mancuso, R.; Mehta, S.; Gabriele, B.; Salerno, G.; Jenks, W. S.; Larock, R. C. J. Org. Chem. 2009, 75, 897.
[26] Du, J. Y.; Ma, Y. H.; Yuan, R. Q.; Nie, S. Z.; Ma, C. L.; Li, C. Z.; Zhao, C. Q. Org. Lett. 2018, 20, 477.
[27] Jung, Y.; Singh, D. K.; Kim, I. Beilstein. J. Org. Chem. 2016, 12, 2689.
[28] Warner, A. J.; Churn, A.; McGough, J. S.; Ingleson, M. J. Angew. Chem., Int. Ed. 2017, 56, 354.
[29] Verma, A. K.; Rustagi, V.; Aggarwal, T.; Singh, A. P. J. Org. Chem. 2010, 75, 7691.
[30] Park, J. H.; Bhilare, S. V.; Youn, S. W. Org. Lett. 2011, 13, 2228.
[31] Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K. Org. Lett. 2006, 8, 5517.
[32] Kanazawa, C.; Terada, M. Tetrahedron Lett. 2007, 48, 933.
[33] Mancuso, R.; Pomelli, C. C.; Malafronte, F.; Maner, A.; Marino, N.; Chiappe, C.; Gabriele, B. Org. Biomol. Chem. 2017, 15, 4831.
[34] (a) Zheng, Y. N.; Liu, M. L.; Qiu, G. Y. S.; Xie, W. L.; Wu, J. Tetrahedron 2019, 75, 1663.
(b) Wang, Y. H.; Qiu, G. Y. S.; Zhou, H. W.; Xie, W. L.; Liu, J. B. Tetrahedron 2019, 75, 3850.
[35] Schlemmer, C.; Andernach, L.; Schollmeyer, D.; Straub, B. F.; Opatz, T. J. Org. Chem. 2012, 77, 10118.
[36] Mehta, S.; Yao, T.; Larock, R. C. J. Org. Chem. 2012, 77, 10938.
[37] (a) Wang, R. X.; Yuan, S. T.; Liu, J. B.; Wu, J.; Qiu, G. Y. S. Org. Biomol. Chem. 2018, 16, 4501.
(b) Wang, Y. H.; Ouyang, B.; Qiu, G. Y. S.; Zhou, H. W.; Liu, J. B. Org. Biomol. Chem. 2019, 17, 4335.
[38] Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2008, 74, 1141.
[39] (a) Faizi, D. J.; Davis, A. J.; Meany, F. B.; Blum, S. A. Angew. Chem., Int. Ed. 2016, 55, 14286.
(b)Issaian, A.; Faizi, D. J.; Bailey, J. O.; Mayer, P.; Berionni, G.; Singleton, D. A. Blum, S. A. J. Org. Chem. 2017, 82, 8165.
[40] Xu, J.; Yu, X. X.; Yan, J. X.; Song, Q. L. Org. Lett. 2017, 19, 6292.
[41] (a) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895.
(b) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578.
[42] (a) Yao, T.; Campo, M. A.; Larock, R. C. Org. Lett. 2004, 6, 2677.
(b) Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511.
[43] Li, C. W.; Wang, C. I.; Liao, H. Y.; Chaudhuri, R.; Liu, R. S. J. Org. Chem. 2007, 72, 9203.
[44] Chen, Y.; Huang, C. L.; Liu, X. C.; Perl, E.; Chen, Z. W.; Namgung, J.; Zhang, G.; Hersh, W. H. J. Org. Chem. 2014, 79, 3452.
[45] Alam, K.; Kim, J. G.; Kang, D. Y.; Park, J. K. Adv. Synth. Catal. 2019, 361, 1683.

无过渡金属参与的炔烃环化反应研究进展

Recent Advances in Cyclization Reaction of Alkynes under Transition Metal-Free Conditions

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