Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

doi:10.6023/cjoc202005062

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3354-3361.DOI: 10.6023/cjoc202005062 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；黄乃正院士七十华诞专辑

无机盐碘化钠光促炔烃双碘化

鲁玲玲^a, 李一鸣^a, 姜雪峰^a,b

a 华东师范大学化学与分子工程学院上海市绿色化学与化工过程绿色化重点实验室上海 200062;
b 南开大学化学学院元素有机化学国家重点实验室天津 300071

收稿日期:2020-05-23 修回日期:2020-06-26 发布日期:2020-07-17
通讯作者: 姜雪峰 E-mail:xfjiang@chem.ecnu.edu.cn
基金资助:
国家重点研发计划（No.2017YFD0200500）、国家自然科学基金（Nos.21971065，21722202，21672069）资助项目.

Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

Lu Lingling^a, Li Yiming^a, Jiang Xuefeng^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2020-05-23 Revised:2020-06-26 Published:2020-07-17
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2017YFD0200500), and the National Natural Science Foundation of China (Nos. 21971065, 21722202, 21672069).

1. cjoc202005062.pdf(1906KB)

Abstract

1,2-Diiodoalkenes can be used as precursors for synthesis of functional molecules such as heterocyclic drugs and organic conjugated materials due to their derivability of functional groups. Herein, alkynes can be converted into 1,2-trans-diiodioalkenes efficiently and conveniently by using inexpensive and stable sodium iodide as iodine source and air as oxidant under the visible-light (blue light) with normal temperature and atmospheric pressure. The corresponding reactions were operated under mild conditions with inexpensive and easily accessible reagents, which obviate the need of transition-metal-catalysts or oxidizing reagents. Meanwhile, this method is compatible with a wide range of substrates, including terminal and internal alkynes even the peptide and carbohydrates containing a variety of heteroatoms and active hydrogen.

Key words: 1,2-diiodoalkenes, alkynes, diiodination, visible-light

Cite this article

Lu Lingling, Li Yiming, Jiang Xuefeng. Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3354-3361.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Seechurn, C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
(b) Piontek, A.; Bisz, E.; Szostak, M. Angew. Chem., Int. Ed. 2018, 57, 11116.
(c) King, A. O.; Yasuda, N. In Organometallics in Process Chemistry, Springer, Berlin, 2004, pp. 205~245.
(d) Ian, W. Ph.D. Dissertation, Durham University, Durham, 2011.
(e) Zeng, X.; Liu, S.; Yang, Y.; Yang, Yi; Hammond, G. B.; Xu, B. Chem 2020, 6, 1018.
[2] (a) Zani, L.; Dessì, A.; Franchi, D.; Calamante, M.; Reginato, G.; Mordini, A. Coord. Chem. Rev. 2019, 392, 177.
(b) Kawabata, K.; Saito, M.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2016, 138, 7725.
(c) Furukawa, S.; Yasuda, T. J. Mater. Chem. A 2019, 7, 14806.
(d) Chen, L.; Zeng, M.; Weng, C.; Tan, S.; Shen, P. ACS Appl. Mater. Interfaces 2019, 11, 48134.
(e) Tovar, J. D. Synthesis 2011, 2387.
(f) Olla, T.; Ibraikulov, O. A.; Ferry, S.; Boyron, O.; Méry, S.; Heinrich, B.; Heiser, T.; Lévêque, P.; Leclerc, N. Macromolecules 2019, 52, 8006.
[3] (a) Atzrodt, J.; Derdau, V.; Fey, T.; Zimmermann, J. Angew. Chem., Int. Ed. 2007, 46, 7744.
(b) Liu, C.; Chen, Z.; Su, C.; Zhao, X.; Gao, Q.; Ning, G.-H.; Zhu, H.; Tang, W.; Leng, K.; Fu, W.; Tian, B.; Peng, X.; Li, J.; Xu, Q.-H.; Zhou, W.; Loh, K. P. Nat. Commun. 2018, 9, 80.
[4] (a) Welch, M. J.; Redvanly, C. S. In The Hand Book of Radiopharmaceuticals: Radiochemistry and Applications, Ed.:Finn, R., Wiley, New York, 2003, p. 423.
(b) Hallouard, F.; Anton, N.; Choquet, P.; Constantinesco, A.; Vandamme, T. Biomaterials 2010, 31, 6249.
(c) Zimprich, F.; Rath, J.; Mauritz, M.; Zulehner, G.; Hilfer, Eva.; Cetin, H.; Kasprian, G.; Auff, E. J. Neurol. 2017, 264, 1209.
[5] (a) Gkotsi, D. S.; Ludewig, H.; Sharma, S. V.; Connolly, J. A.; Dhaliwal, J.; Wang, Y.; Unsworth, W. P.; Taylor, R. J. K.; McLachlan, M. M. W.; Shanahan, S.; Naismith, J. H.; Goss, R. J. M. Nat. Chem. 2019, 11, 1091.
(b) Butler, A.; Sandy, M. Nature 2009, 460, 848.
(c) Latham, J.; Brandenburger, E.; Shepherd, A.; Menon, B. R. K.; Micklefield, J. Chem. Rev. 2018, 118, 232.
[6] Li, Y.; Mou, T.; Lu, L.; Jiang, X. Chem. Commun., 2019, 55, 14299.
[7] (a) Banerjee, S.; Khatri, H.; Balasanthiran, V.; Koodali, R. T.; Sereda, G. Tetrahedron 2011, 67, 5717.
(b) Ranu, B. C.; Adak, L.; Chattopadhyay, K. J. Org. Chem. 2008, 73, 5609.
(c) Kimura, T.; Nishimura, Y.; Ishida, N.; Momochi, H.; Yamashita, H.; Satoh, T. Tetrahedron Lett. 2013, 54, 1049.
[8] (a) Bao, Y.; Yang, X.; Zhou, Q.; Yang, F. Org. Lett. 2018, 20, 1966.
(b) Lin, Y.; Lu, G.; Cai, C.; Yi, W. Org. Lett. 2015, 17, 3310.
[9] Li, J. H.; Tang, S. Synth. Commun. 2005, 35, 105.
[10] (a) Liang, Y.; Tao, L.-M.; Zhang, Y.-H.; Li, J.-H. Synthesis 2008, 3988.
(b) Raff, G.; Belot, S.; Balme, G.; Monteiro, N. Org. Biomol. Chem. 2011, 9, 1474.
[11] Schuh, K.; Glorius, F. Synthesis 2007, 2297.
[12] Shen, G.; Yang, B.; Huang, X.; Hou, Y.; Gao, H.; Cui, J.; Cui, C.; Zhang, T. J. Org. Chem. 2017, 82, 3798.
[13] Woodward, S.; Ackermann, M.; Ahirwar, S. K.; Burroughs, L.; Garrett, M. R.; Ritchie, J.; Shine, J.; Tyril, B.; Simpson, K.; Woodward, P. Chem. Eur. J. 2017, 3, 7819.
[14] (a) Sun, A.; Lauher, J. W.; Goroff, N. S. Science 2006, 312, 1030.
(b) DeCicco, R. C.; Luo, L.; Goroff, N. S. Acc. Chem. Res. 2019, 52, 2080.
[15] Terent'ev, A. O.; Borisov, D. A.; Krylov, I. B.; Nikishin, G. I. Synth. Commun. 2007, 37, 3151.
[16] (a) Dolbier, W. R.; Duan, J.-X.; Chen, Q.-Y. J. Org. Chem. 1998, 63, 9486.
(b) Li, J.-H.; Tang, S. Synth. Commun. 2005, 35, 105.
(c) Su, L.; Lei, C.-Y.; Fan, W.-Y.; Liu, L.-X. Synth. Commun. 2011, 41, 1200.
[17] (a) Li, J.-H.; Xie, Y.-X.; Yin, D.-L. Green Chem. 2002, 4, 505.
(b) Larson, S.; Luidhardt, T.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1988, 29, 35.
(c) Song, S.; Li, X.; Wei, J.; Wang, W.; Zhang, Y.; Ai, L.; Zhu, Y.; Shi, X.; Zhang, X.; Jiao, N. Nat. Catal. 2020, 3, 107.
[18] Banothu, R.; Peraka, S.; Kodumuri, S.; Chevella, D.; Gajula, K. S.; Amrutham, V.; Yennamaneni, D. R.; Nama, N. New J. Chem. 2018, 42, 17879.
[19] Stavber, S.; Stavber, G.; Iskra, J.; Zupan, M. Adv. Synth. Catal. 2008, 350, 2921.
[20] Guo, C.-C.; Jiang, Q.; Wang, J.-Y. Synthesis 2015, 47, 2081.
[21] (a) Liu, Y.; Maruoka, K.; Huang, D.-Y.; Huang, J. J. Org. Chem. 2017, 82, 11865.
(b) Kashyap, S.; Rao D. S.; Reddy, T. R. Org. Biomol. Chem. 2018, 16, 1508.
[22] Madabhushi, S.; Jillella, R.; Mallu, K. K. R.; Golada, K. R.; Vangipuram, V. S. Tetrahedron Lett. 2013, 54, 3993.
[23] Yang, F.; Jin, T.; Bao, M.; Yamamoto, Y. Chem. Commun. 2011, 47, 4013.

无机盐碘化钠光促炔烃双碘化

Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[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]	Min Wu, Bo Liu, Jialong Yuan, Qiang Fu, Rui Wang, Dawei Lou, Fushun Liang. Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2269-2292.
[4]	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.
[5]	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.
[6]	Changyuan Du, Yucai Tang, Jinglin Duan, Biyu Yang, Yupeng He, Qian Zhou, Xuewen Liu. Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4268-4276.
[7]	Juan Tang, Jiayu Hu, Zhiqiang Zhu, Shouzhi Pu. Recent Advances in Visible-Light-Induced Organic Phosphine- Promoted Deoxygenative Functionalization Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4036-4056.
[8]	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.
[9]	Panpan Lei, Qinlin Chen, Hang Chen, Yang Zhou, Linhai Jin, Wei Wang, Fener Chen. Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 254-264.
[10]	Zhentao Pan, Tong Liu, Yongmin Ma, Jianbo Yan, Ya-Jun Wang. Construction of Quinazolin(thi)ones by Brønsted Acid/Visible-Light Photoredox Relay Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2823-2831.
[11]	Haoyang Liu, Shuangshuang Sun, Xianli Ma, Yanyan Chen, Yanli Xu. Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2867-2876.
[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]	Ruisheng Liu, Shuangmin Fu, Xiumin Chu, Lingli Zhang, Rou Ding, Xian'en Zhao, Huilan Yue, Wei Wei. Visible-Light-Induced Denitrification Oxygenation Reaction of α-Diazoesters to Construct α-Oxyimido Esters [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2462-2470.
[14]	Runye Gao, Lingling Zuo, Fang Wang, Chuanying Li, Huajiang Jiang, Pinhua Li, Lei Wang. Recent Advances in Controllable Organic Reactions Induced by Visible Light without External Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1883-1903.
[15]	Jiayu Hu, Zhiqiang Zhu, Zongbo Xie, Zhanggao Le. Recent Advances in Visible-Light-Induced Decarboxylative Coupling Reactions of α-Amino Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 978-1001.