Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes

doi:10.6023/cjoc201711050

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1172-1176.DOI: 10.6023/cjoc201711050 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

Articles

以炔为原料可调控合成碘代炔和二碘代烯烃

陈锁^a, 章晓炜^a, 赵辉^b, 郭晓红^a, 胡祥国^a

a 江西师范大学国家单糖化学合成工程技术研究中心南昌 330022;
b 安徽省应用技术研究院有效成分提取分离研究中心合肥 230031

收稿日期:2017-11-30 修回日期:2018-01-08 发布日期:2018-01-26
通讯作者: 章晓炜,E-mail:xwzhang@jxnu.edu.cn;胡祥国,E-mail:huxiangg@iccas.ac.cn E-mail:xwzhang@jxnu.edu.cn;huxiangg@iccas.ac.cn
基金资助:
国家自然科学基金（No.21502076）、合肥市百人计划、江西省杰出青年人才计划（No.20171BCB23039）资助项目.

Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes

Chen Suo^a, Zhang Xiaowei^a, Zhao Hui^b, Guo Xiaohong^a, Hu Xiangguo^a

a National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022;
b Anhui Engineering Technology Research Center for Extraction and Isolation of Active Components, Anhui Academy of Applied Technology, Hefei 230031

Received:2017-11-30 Revised:2018-01-08 Published:2018-01-26
Contact: 10.6023/cjoc11050 E-mail:xwzhang@jxnu.edu.cn;huxiangg@iccas.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502076), the Hundred-Talent Program of Hefei City and the Outstanding Young Talents Scheme of Jiangxi Province (No. 20171BCB23039).

1. Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes.PDF(807KB)

Abstract

Iodoalkynes and diiodoalkenes are valuable intermediates used extensively for C—C, C—O and C—N bonds formation. Therefore, the development of new method for the synthesis of these compunds is desirable. In this work, a novel and switchable protocol for the synthesis of iodoalkynes and diiodoalkenes has been developed, which were formed from terminal alkynes using the same reagent system of ZnI₂ and tert-butyl nitrite in the presence or absence of triethylamine, respectively. The iodoalkyne formation is operationally simple, mild (weak base and room temperature), and tolerant of a large range of functional groups. In contrast, the diiodoalkene transformation shows interesting dependence on the electron property, and only electron-rich and neutral compounds are viable substrates. The control experiments performed suggest that iodoalkynes and diiodoalkenes are not interchangeable under a series of reaction conditions, including the optimized conditions, which can be explained by the mechanism in which both of the reactions involve a iodonium intermediate formed directly from a terminal alkyne.

Key words: iodoalkyne, diiodoalkene, tert-butyl nitrite, alkyne, zinc iodide

Cite this article

Chen Suo, Zhang Xiaowei, Zhao Hui, Guo Xiaohong, Hu Xiangguo. Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes[J]. Chin. J. Org. Chem., 2018, 38(5): 1172-1176.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wu, W. Q.; Jiang, H. F. Acc. Chem. Res. 2014, 47, 2483.
[2] Jeffery, T. J. Chem. Soc., Chem. Commun. 1988, 909.
[3] Casarini, A.; Dembech, P.; Reginato, G.; Ricci, A.; Seconi, G. Tetrahedron Lett. 1991, 32, 2169.
[4] Rao, M. L. N.; Periasamy, M. Synth. Commun. 1995, 25, 2295.
[5] Monenschein, H.; Sourkouni-Argirusi, G.; Schubothe, K. M.; O'Hare, T.; Kirschning, A. Org. Lett. 1999, 1, 2101.
[6] Nishiguchi, I.; Kanbe, O.; Itoh, K.; Maekawa, H. Synlett 2000, 89.
[7] Abele, E.; Fleisher, M.; Rubina, K.; Abele, R.; Lukevics, E. J. Mol. Catal. A:Chem. 2001165, 121.
[8] Lahrache, H.; Robin, S.; Rousseau, G. Tetrahedron Lett. 2005, 46, 1635.
[9] Stefani, H. A.; Cella, R.; Dörr, F. A.; Pereira, C. M. P.; Gomes, F. P.; Zeni, G. Tetrahedron Lett. 2005, 46, 2001.
[10] Yan, J.; Li, J. H.; Cheng, D. P. Synlett 2007, 2442.
[11] Meng, L. G.; Cai, P. J.; Guo, Q. X.; Xue, S. Synth. Commun. 2008, 38, 225.
[12] Chen, S. N.; Lin, T. C.; Hung, T. T.; Tsai, F. Y. J. Chin. Chem. Soc. 2009, 56, 1078.
[13] Reddy, K. R.; Venkateshwar, M.; Maheswari, C. U.; Kumar, P. S. Tetrahedron Lett. 2010, 51, 2170.
[14] Nosel, P.; Lauterbach, T.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Chem. Eur. J. 2013, 19, 8634.
[15] Nouzarian, M.; Hosseinzadeh, R.; Golchoubian, H. Synth. Commun. 2013, 43, 2913.
[16] Li, M. R.; Li, Y. J.; Zhao, B. Z.; Liang, F. S.; Jin, L. Y. RSC Adv. 2014, 4, 30046.
[17] Chowdhury, R. M.; Wilden, J. D. Org. Biomol. Chem. 2015, 13, 5859.
[18] Gómez-Herrera, A.; Nahra, F.; Brill, M.; Nolan, S. P.; Cazin, C. S. J. ChemCatChem 2016, 8, 3381.
[19] Karpov, G. V.; Popik, V. V. J. Am. Chem. Soc. 2007, 129, 3792.
[20] Barsoum, D. N.; Okashah, N.; Zhang, X. G.; Zhu, L. J. Org. Chem. 2015, 80, 9542.
[21] Chen, W. W.; Zhang, J. L.; Wang, B.; Zhao, Z. X.; Wang, X. Y.; Hu, Y. F. J. Org. Chem. 2015, 80, 2413.
[22] Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018.
[23] Wilkins, L. C.; Lawson, J. R.; Wieneke, P.; Rominger, F.; Hashmi, A. S. K.; Hansmann, M. M.; Melen, R. L. Chem. Eur. J. 2016, 22, 14618.
[24] He, G. W.; Liu, F. W.; Xu, X. H. Chin. J. Org. Chem. 2007, 27, 663(in Chinese). (贺干武, 刘凤伟, 许新华, 有机化学, 2007, 27, 663.)
[25] Larson, S.; Luidhardt, T.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1988, 29, 35.
[26] Hondrogiannis, G.; Lee, L. C.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1989, 30, 2069.
[27] Barluenga, J.; Rodriguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104.
[28] Henaff, N.; Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1997, 38, 4525.
[29] Duan, J. X.; Dolbier, W. R.; Jr.; Chen, Q. Y. J. Org. Chem. 1998, 63, 9486.
[30] Hénaff, N.; Whiting, A. J. Chem. Soc., Perkin Trans. 12000, 395.
[31] Li, J. H.; Xie, Y. X.; Yin, D. L. Green Chem. 2002, 4, 505.
[32] Li, J. H.; Xie, Y. X.; Yin, D. L.; Jiang, H. F. Chin. J. Chem. 2003, 21, 714.
[33] Jereb, M.; Zupan, M.; Stavber, S. Chem. Commun. 2004, 2614.
[34] Pavlinac, J.; Zupan, M.; Stavber, S. Org. Biomol. Chem. 2007, 5, 699.
[35] Terent'ev, A. O.; Borisov, D. A.; Krylov, I. B.; Nikishin, G. I. Synth. Commun. 2007, 37, 3151.
[36] Tveryakova, E. N.; Miroshnichenko, Y. Y.; Perederina, I. A.; Yusubov, M. S. Russ. J. Org. Chem. 2007, 43, 152.
[37] Stavber, G.; Iskra, J.; Zupan, M.; Stavber, S. Adv. Synth. Catal. 2008, 350, 2921.
[38] Guo, C. C.; Jiang, Q.; Wang, J. Y. Synthesis 2015, 47, 2081.
[39] Lin, Y. M.; Lu, G. P.; Cai, C.; Yi, W. B. Org. Lett. 2015, 17, 3310.
[40] Tang, S.; Liu, K.; Long, Y.; Qi, X. T.; Lan, Y.; Lei, A. W. Chem. Commun. 2015, 51, 8769.
[41] Wu, Y. M.; Zhang, J. M.; Guo, Y. W.; Wang, X. J.; Zhu, Z. T. Synlett 2016, 27, 2259.
[42] Li, J.H.; Xie, J. X; Yin, D. L. Chin. J. Org. Chem. 2002, 22, 894(in Chinese). (李金恒, 谢叶香, 尹笃林, 有机化学, 2002, 22, 894.)
[43] Yu, K.; Zhang, X.; Hu, Q.; Liu, L. Chin. J. Org. Chem. 2010, 30, 266(in Chinese). (余开辉, 张小丽, 胡乔生, 刘良先, 有机化学, 2010, 30, 266.)
[44] For selected example of synthesis of diiodoalkynes from intermal alkynes, see:(a) Su, L.; Lei, C.-Y.; Fan, W.-Y.; Liu, L.-X. Synth. Commun. 2011, 41, 1200.
(b) Liu, Y.; Huang, D.; Huang, J.; Maruoka, K. J. Org. Chem. 2017, 82, 11865.
[45] Liu, Y. Synlett 2011, 1184.
[46] Dutta, U.; Maity, S.; Kancherla, R.; Maiti, D. Org. Lett. 2014, 16, 6302.
[47] Dutta, U.; Lupton, D. W.; Maiti, D. Org. Lett. 2016, 18, 860.
[48] (a) Oliver, D.; Dino, W.; Nils, T.; Nancy, G.; Francois, D. Org. Lett. 2014, 16, 4722.
(b) Pelletier, G.; Lie, S.; Mousseau, J. J.; Charette, A. B. Org. Lett. 2012, 14, 5464.
(c) Dan, L.; Joaquin, M. A.; Emil, B. L.; William, R. D. Chem. Eur. J. 2015, 21, 18122.
(d) Madabhushi, S.; Jillella, R.; R.Mallu, K. K.; Godala, K. R.; Vangipuram, V. S. Tetrahedron Lett. 2013, 54, 3993.
(e) Abe, H.; Suzuki, H. Bull. Chem. Soc. Jpn. 1999, 72, 787.

以炔为原料可调控合成碘代炔和二碘代烯烃

Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[3]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[4]	Suzhen Zhang, Wenwen Zhang, Hui Yang, Qing Gu, Shuli You. Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2926-2933.
[5]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[6]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[7]	Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760.
[8]	Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.
[9]	Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang. Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1559-1565.
[10]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[11]	Chong Tian, Qi Sun, Junfeng Wang, Qiao Chen, Zhiguo Wen, Maxim Borzov, Wanli Nie. E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^– [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 338-344.
[12]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[13]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[14]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.
[15]	Huili Liu, Chaojie Zhu, Tiandi Tang. Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1792-1798.