Citation: Xuelun Duan, Nan Zheng, Ming Li, Xinhao Sun, Zhuye Lin, Pan Qiu, Wangze Song. Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes[J]. Chinese Chemical Letters, ;2021, 32(12): 4019-4023. doi: 10.1016/j.cclet.2021.05.037 shu

Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes

State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Department of Pharmaceutical Science, Dalian University of Technology, Dalian 116024, China

nzheng@dlut.edu.cn

wzsong@dlut.edu.cn

Received Date: 1 April 2021
Revised Date: 16 May 2021
Accepted Date: 16 May 2021
Available Online: 25 May 2021

Figures(5)

Remote ether groups could be used as directing groups to prepare fully substituted 5-ether-1,2,3-triazoles with exclusive 1,5-regioselectivities and excellent chemoselectivities. Ether group could coordinate with iridium catalyst by lone-pair electron at a distance (up to four σ bonds) away from alkyne to control the regioselectivity by weak coordination effect. The cycloaddition reaction chemoselectively occurred at the propargyl ether moiety of diyne to give unique fully substituted 4-alkynyl-triazole.
- Remote ether,
- Directing group,
- Regioselectivity,
- Chemoselectivity,
- Triazole
1. [1]
  R.L. Reyes, M. Sato, T. Iwai, et al., Science 369 (2020) 970-974. doi: 10.1126/science.abc8320
2. [2]
  R.A. Johnson, K.B. Sharpless, Catalytic Asymmetric Synthesis, 2nd ed., Wiley, New York, 2005.
3. [3]
  Z. Li, H. Yamamoto, Acc. Chem. Res. 46 (2013) 506-508. doi: 10.1021/ar300216r
4. [4]
  G. Li, D. Leow, L. Wan, J.Q. Yu, Angew. Chem. Int. Ed. 52 (2013) 1245-1247. doi: 10.1002/anie.201207770
5. [5]
  Á. Iglesias, R. Álvarez, Á. R. de Lera, K. Muñiz, Angew. Chem. Int. Ed. 51 (2012) 2225-2228. doi: 10.1002/anie.201108351
6. [6]
  C.W. Liskey, J.F. Hartwig, J. Am. Chem. Soc. 134 (2012) 12422-12425. doi: 10.1021/ja305596v
7. [7]
  J. Oyamada, M. Nishiura, Z. Hou, Angew. Chem. Int. Ed. 50 (2011) 10720-10723. doi: 10.1002/anie.201105636
8. [8]
  S. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura, J. Am. Chem. Soc. 131 (2009) 5058-5059. doi: 10.1021/ja9008419
9. [9]
  G.J. Choi, Q. Zhu, D.C. Miller, C.J. Gu, R.R. Knowles, Nature 539 (2016) 268-271. doi: 10.1038/nature19811
10. [10]
  X.C. Wang, W. Gong, L.Z. Fang, et al., Nature 519 (2015) 334-338. doi: 10.1038/nature14214
11. [11]
  D. Leow, G. Li, T.S. Mei, J.Q. Yu, Nature 486 (2012) 518-522. doi: 10.1038/nature11158
12. [12]
  G. He, G.A. Chen, Angew. Chem. Int. Ed. 50 (2011) 5192-5196. doi: 10.1002/anie.201100984
13. [13]
  H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40 (2001) 2004-2021. doi: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
14. [14]
  C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67 (2002) 3057-3064. doi: 10.1021/jo011148j
15. [15]
  V.V. Rostovtssev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41 (2002) 2596-2599. doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
16. [16]
  B.T. Worrell, J.A. Malik, V.V. Fokin, Science 340 (2013) 457-460. doi: 10.1126/science.1229506
17. [17]
  J. Miguel-Ávila, M. Tomás-Gamasa, A.P. Olmos, J. Pérez, J.L. Mascareñas, Chem. Sci. 9 (2018) 1947-1952. doi: 10.1039/C7SC04643J
18. [18]
  P. Destito, J.R. Couceiro, H. Faustino, F. López, J.L. Mascareñas, Angew. Chem. Int. Ed. 56 (2017) 10766-10770. doi: 10.1002/anie.201705006
19. [19]
  S. Ding, G. Jia, J. Sun, Angew. Chem. Int. Ed. 53 (2014) 1877-1880. doi: 10.1002/anie.201309855
20. [20]
  Q. Luo, G. Jia, J. Sun, Z. Lin, J. Org. Chem. 79 (2014) 11970-11980. doi: 10.1021/jo5018348
21. [21]
  W.G. Kim, M.E. Kang, J.B. Lee, et al., J. Am. Chem. Soc. 139 (2017) 12121-12124. doi: 10.1021/jacs.7b06338
22. [22]
  W.G. Kim, S.Y. Baek, S.Y. Jeong, et al., Org. Biomol. Chem. 18 (2020) 3374-3381. doi: 10.1039/D0OB00579G
23. [23]
  L. Zeng, Z. Lai, C. Zhang, H. Xie, S. Cui, Org. Lett. 22 (2020) 2220-2224. doi: 10.1021/acs.orglett.0c00394
24. [24]
  R. Chen, L. Zeng, Z. Lai, S. Cui, Adv. Synth. Catal. 361 (2019) 989-994. doi: 10.1002/adsc.201801410
25. [25]
  M. Li, N. Zheng, J. Li, Y. Zheng, W. Song, Green Chem 22 (2020) 2394-2398. doi: 10.1039/D0GC00555J
26. [26]
  W. Song, N. Zheng, M. Li, et al., Org. Lett. 20 (2018) 6705-6709. doi: 10.1021/acs.orglett.8b02794
27. [27]
  W. Song, N. Zheng, Org. Lett. 19 (2017) 6200-6203. doi: 10.1021/acs.orglett.7b03123
28. [28]
  W. Song, M. Li, K. Dong, Y. Zheng, Adv. Synth. Catal. 361 (2019) 5258-5263. doi: 10.1002/adsc.201901014
29. [29]
  W. Song, N. Zheng, M. Li, et al., Adv. Synth. Catal. 361 (2019) 469-475. doi: 10.1002/adsc.201801216
30. [30]
  W. Song, N. Zheng, M. Li, K. Ullah, Y. Zheng, Adv. Synth. Catal. 360 (2018) 2429-2434. doi: 10.1002/adsc.201800336
31. [31]
  M. Li, K. Dong, Y. Zheng, W. Song, Org. Biomol. Chem. 17 (2019) 9933-9941. doi: 10.1039/C9OB02081K
32. [32]
  Y. Liao, Q. Lu, G. Chen, et al., ACS Catal. 7 (2017) 7529-7534. doi: 10.1021/acscatal.7b02558
33. [33]
  Y. Chen, L. Liu, D. Wu, Y.P. He, A. Li, Chin. Chem. Lett. 30 (2019) 269-270. doi: 10.1016/j.cclet.2018.06.001
34. [34]
  R. Peng, Y. Xu, Q. Cao, Chin. Chem. Lett. 29 (2018) 1465-1474. doi: 10.1016/j.cclet.2018.09.001
35. [35]
  B.C. Boren, S. Narayan, L.K. Rasmussen, et al., J. Am. Chem. Soc. 130 (2008) 8923-8930. doi: 10.1021/ja0749993
36. [36]
  M.M. Majireck, S.M. Weinreb, J. Org. Chem. 71 (2006) 8680-8683. doi: 10.1021/jo061688m
37. [37]
  P.C. Knutson, H.E. Fredericks, E.M. Ferreira, Org. Lett. 20 (2018) 6845-6849. doi: 10.1021/acs.orglett.8b02975
38. [38]
  P. Wu, V.V. Fokin, Aldrichimica Acta 40 (2007) 7-17.
39. [39]
  M. Meldal, C.W. Tormøe, Chem. Rev. 108 (2008) 2952-3015. doi: 10.1021/cr0783479
40. [40]
  J.E. Moses, A.D. Moorhouse, Chem. Soc. Rev. 36 (2007) 1249-1262. doi: 10.1039/B613014N
41. [41]
  J.E. Hein, V.V. Fokin, Chem. Soc. Rev. 39 (2010) 1302-1315. doi: 10.1039/b904091a
42. [42]
  C. Wang, D. Ikhlef, S. Kahlal, J.Y. Saillard, D. Astruc, Coordin. Chem. Rev. 316 (2016) 1-20. doi: 10.1016/j.ccr.2016.02.010
43. [43]
  T. Henkel, R.M. Brunne, H. Müller, F. Reichel, Angew. Chem. Int. Ed. 38 (1999) 643-647. doi: 10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO;2-G
44. [44]
  A. Srivastava, L. Aggarwal, N. Jain, ACS Comb. Sci. 17 (2015) 39-48. doi: 10.1021/co500135z
45. [45]
  A. Dell'Isola, M.M.W. McLachlan, B.W. Neuman, et al., Chem. Eur. J. 20 (2014) 11685-11689. doi: 10.1002/chem.201403560
46. [46]
  B. Banerji, S.K. Pramanik, P. Sanphui, S. Nikhar, S.C. Biswas, Chem. Biol. Drug Des. 82 (2013) 401-409. doi: 10.1111/cbdd.12164
47. [47]
  C.S. Sevov, J.F. Hartwig, J. Am. Chem. Soc. 136 (2014) 10625-10631. doi: 10.1021/ja504414c
48. [48]
  C.S. Sevov, J.F. Hartwig, J. Am. Chem. Soc. 135 (2013) 9303-9306. doi: 10.1021/ja4052153
1. [1]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
2. [2]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
3. [3]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
4. [4]
  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
5. [5]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
6. [6]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
7. [7]
  Yue Mao , Zhonghang Chen , Tiankai Sun , Wenyue Cui , Peng Cheng , Wei Shi . Luminescent coordination polymers with mixed carboxylate and triazole ligands for rapid detection of chloroprene metabolite. Chinese Journal of Structural Chemistry, 2024, 43(9): 100353-100353. doi: 10.1016/j.cjsc.2024.100353
8. [8]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
9. [9]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
10. [10]
  Xiao Zhu , Yanbing Mo , Jiawei Chen , Gaopan Liu , Yonggang Wang , Xiaoli Dong . A weakly-solvated ether-based electrolyte for fast-charging graphite anode. Chinese Chemical Letters, 2024, 35(8): 109146-. doi: 10.1016/j.cclet.2023.109146
11. [11]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
12. [12]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
13. [13]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
14. [14]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
15. [15]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
16. [16]
  Junchen Peng , Xue Yin , Dandan Dong , Zhongyuan Guo , Qinqin Wang , Minmin Liu , Fei He , Bin Dai , Chaofeng Huang . Promotion effect of epoxy group neighboring single-atom Cu site on acetylene hydrochlorination. Chinese Chemical Letters, 2024, 35(6): 109508-. doi: 10.1016/j.cclet.2024.109508
17. [17]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
18. [18]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
19. [19]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
20. [20]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(454)
HTML views(53)

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