Citation: Li Xiuying, Li Yajun, Wei Xiansheng, Luo Jinrong, Huang Guobao, Tan Minxiong. Recent Progress on Reactions of Arylmethyl Azides with Alkenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1831-1836. doi: 10.6023/cjoc201903001 shu

Recent Progress on Reactions of Arylmethyl Azides with Alkenes

Li Xiuying ^a,† ,
Li Yajun ^b,† ,
Wei Xiansheng ^a ,
Luo Jinrong ^a ,
Huang Guobao ^a,, ,
Tan Minxiong ^a,,

a.
Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science of Yulin Normal University, Yulin 537000
b.
College of Medicine & Technology, Hunan Polytechnic of Environment and Biology, Hengyang 421005

Corresponding author: Huang Guobao, lzjx0915@163.com Tan Minxiong, tanmx00@163.com

^†

Received Date: 1 March 2019
Revised Date: 30 March 2019
Available Online: 16 July 2019
Fund Project: the Yulin Normal University Research 201810606010Project supported by the National Natural Science Foundation of China (No. 21761033), the Natural Science Foundation of Guangxi (Nos. 2017GXNSFBA198211, 2018GXNSFAA294064), and the Yulin Normal University Research (Nos. 2018YJKY36, 201810606010)the National Natural Science Foundation of China 21761033the Yulin Normal University Research 2018YJKY36the Natural Science Foundation of Guangxi 2018GXNSFAA294064the Natural Science Foundation of Guangxi 2017GXNSFBA198211

Figures(11)

Arylmethyl azides (ArCH₂N₃) as one of the significant nitrogen sources with stable properties, simple synthesis, have been widely used in a wide range of organic synthesis reactions. The recent progress (2014~2018) on reactions of arylmethyl azides with alkenes is summarized. In addition, the organic reactions of arylmethyl azides with types of alkenes are described respectively, with their scope of substrates and reaction mechanism. It is hoped that this review can be referred to the future application in organic synthesis of arylmethyl azides with alkenes.
- arylmethyl azides,
- alkenes,
- reaction mechanism
1. [1]
  Grecianl, S.; Aubé, J. Organic Azides: Syntheses and Applications, Vol. 7, Eds.: Bräse, S.; Banert, K., John Wiley & Sons, Ltd, Chichester, UK, 2010, pp. 191~310.
2. [2]
  (a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
  (b) Lee, J. H.; Gupta, S.; Jeong, W.; Rhee, Y. H.; Park, J. Angew. Chem., Int. Ed. 2012, 51, 10851.
  (c) Han, J.; Jeon, M.; Pak, H. K.; Rhee, Y. H.; Park, J. Adv. Synth. Catal. 2014, 356, 2769.
  (d) Gupta, S.; Han, J.; Kim, Y.; Lee, S. W.; Rhee, Y. H.; Park. J. J. Org. Chem. 2014, 79, 9094.
  (e) Chou, H.-H.; Raines, R. T. J. Am. Chem. Soc. 2013, 135, 14936.
  (f) Zhang, X.-X.; Sun, X.-P.; Zhang, H.-F.; Cui, X.-L.; Ma, M.-T. Chin. J. Org. Chem. 2015, 35, 1469(in Chinese).
  (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.)
  (g) Zhang, W.-S.; Xu, W.-J.; Kuang, C.-X. Chin. J. Org. Chem. 2015, 35, 2059(in Chinese).
  (张文生, 许文静, 匡春香, 有机化学, 2015, 35, 2059.)
3. [3]
  (a) Song, Z.-Q.; Zhao, Y.-M.; Zhai, H.-B. Org. Lett. 2011, 13, 6331.
  (b) Lamani, M.; Devadig, P.; Prabhu, K. R. Org. Biomol. Chem. 2012, 10, 2753.
  (c) Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S.; Gettongsong, T. Org. Biomol. Chem. 2013, 11, 1463.
4. [4]
  Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040. doi: 10.1021/acs.accounts.5b00020
5. [5]
  Li, J.-L.; Wang, Y.-C.; Li, W.-Z.; Wang, H.-S.; Mo, D.-L.; Pan, Y.-M. Chem. Commun. 2015, 51, 17772. doi: 10.1039/C5CC06487B
6. [6]
  Tummatorn, J.; Poonsilp, P.; Nimnual, P.; Janprasit, J.; Thongsornkleeb, C.; Ruchirawat, S. J. Org. Chem. 2015, 80, 4516. doi: 10.1021/acs.joc.5b00375
7. [7]
  Wang, Y.-C.; Li, J.-L.; He, Y.; Xie, Y.-Y.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2015, 357, 3229. doi: 10.1002/adsc.201500584
8. [8]
  Wang, Y.-C.; Xie, Y.-Y.; Qu, H.-E.; Wang, H.-S.; Pan, Y.-M.; Huang, F. -P. J. Org. Chem. 2014, 79, 4463. doi: 10.1021/jo5004339
9. [9]
  Zefirov, N. S.; Chapovskaya, N. K.; Kolesnikov, V. V. Chem. Commun. 1971, 1001.
10. [10]
  Piet, J. C.; Le H. G.; Cailleux, P.; Benhaoua, H.; Carrie, R. Bull. Soc. Chim. Belg. 1996, 105, 33.
11. [11]
  Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Zunino, E.; Vaccaro, L. J. Org. Chem. 2005, 70, 6526. doi: 10.1021/jo0507845
12. [12]
  Wang, Y.-C.; Xie, Y.-Y.; Tan, X.-C.; Wang, H.-S.; Pan, Y.-M. Org. Biomol. Chem. 2015, 13, 513. doi: 10.1039/C4OB01801J
13. [13]
  Donald, A. S. R.; Marks, R. E. J. Chem. Soc. C 1967, 1188. doi: 10.1039/j39670001188
14. [14]
  Casey, M.; Donnelly, J. A.; Ryan, J. C.; Ushioda, S. ARKIVOC 2003, 7, 310.
15. [15]
  (a) Reddy, D. S.; Judd, W. R.; Aubé, J. Org. Lett. 2003, 5, 3899.
  (b) Silvio, C.; Amenson, T. G. Tetrahedron Lett. 2012, 53, 6710.
16. [16]
  Mahoney, J. M.; Smith, C. R.; Johnston, J. N. J. Am. Chem. Soc. 2005, 127, 1354. doi: 10.1021/ja045608c
17. [17]
  Jumreang, T.; Charnsak, T.; Somsak, R.; Tanita, G. Org. Biomol. Chem. 2013, 11, 1463. doi: 10.1039/c3ob27493d
18. [18]
  Xie, Y.-Y.; Wang, Y.-C.; Qu, H.-E.; Tan, X.-C.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2014, 356, 3347. doi: 10.1002/adsc.201400315
19. [19]
  Gangaprasad, D.; Paul Raj, J.; Kiranmye, T.; Sagubar Sadik, S.; Elangovan, J. RSC Adv. 2015, 5, 63473. doi: 10.1039/C5RA08693K
20. [20]
  Yang, W.-C.; Miao, T.; Li, P.-H.; Wang, L. RSC Adv. 2015, 5, 95833. doi: 10.1039/C5RA16974G
21. [21]
  Gangaprasad, D.; Paul Raj, J.; Kiranmye, T.; Karthikeyan, K.; Elangovan, J. Eur. J. Org. Chem. 2016, 5642.
22. [22]
  Xie, Y.-Y.; Wang, Y.-C.; He, Y.; Hu, D.-C.; Wang, H.-S.; Pan, Y.-M. Green Chem. 2017, 19, 656. doi: 10.1039/C6GC01553K
23. [23]
  Yan, Z.-M.; Wu, N.; Liang, D.; Wang, H.-S.; Pan, Y.-M. Org. Lett. 2014, 16, 4048. doi: 10.1021/ol501930f
1. [1]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
2. [2]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
3. [3]
  Junyuan Zhang , Xiangzheng Ren , Zhiwei Miao . 烯烃1,3-双官能团化反应研究进展. University Chemistry, 2026, 41(8): 148-161. doi: 10.12461/PKU.DXHX202507121
4. [4]
  Ruikang Su , Muyan Bai , Zhiqing Liu , Fang Fang , Yuena Yu . Wittig反应与可见光氧化还原催化融合构建烯烃. University Chemistry, 2026, 41(8): 370-379. doi: 10.12461/PKU.DXHX202507075
5. [5]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
6. [6]
  Chonghang Sun , Xingfang Zheng , Lin Li , Xiaolei Jiang , Fangdong Hu . 类比法在有机化学机理教学中的应用——以羰基化合物及羧酸衍生物为例. University Chemistry, 2026, 41(9): 382-391. doi: 10.12461/PKU.DXHX202508095
7. [7]
  Anqi LI , Wenjing YANG , Xueming LI , Yanfong REN . Performance and mechanism of a foam Ti/FeCo-Fe₂O₃-CoFe₂O₄/SnO₂-Sb anode for synergistic activation of peroxymonosulfate toward degradation of organic pollutants. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 944-958. doi: 10.11862/CJIC.20250323
8. [8]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
9. [9]
  Yang Wang , Shuangliang Liu , Jianbo Zhao . Exploring the mechanism of Diels-Alder reaction: a computational chemistry experiment for undergraduate students. University Chemistry, 2026, 41(7): 257-265. doi: 10.12461/PKU.DXHX202504061
10. [10]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019
11. [11]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
12. [12]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
13. [13]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
14. [14]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
15. [15]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
16. [16]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
17. [17]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
18. [18]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
19. [19]
  Wanping Chen . Construction of Knowledge Logic and Discovery through Reasoning: Summarizing the Reaction Patterns of Reactive Metals with Oxygen. University Chemistry, 2026, 41(2): 95-102. doi: 10.12461/PKU.DXHX202503108
20. [20]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172

Get Citation

PDF

XML

Metrics

PDF Downloads(31)
Abstract views(3973)
HTML views(1024)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142