Citation: Lan Tianlei, Qin Haijuan, Chen Wenting, Liu Wei, Chen Chao. Synthesis and reactivity of carbazole-containing hypervalent iodine(Ⅲ) reagents[J]. Chinese Chemical Letters, ;2020, 31(2): 357-360. doi: 10.1016/j.cclet.2019.07.031 shu

Synthesis and reactivity of carbazole-containing hypervalent iodine(Ⅲ) reagents

Lan Tianlei ^a,b,1 ,
Qin Haijuan ^a,1 ,
Chen Wenting ^c ,
Liu Wei ^a,*, ,
Chen Chao ^b,*,

a.
College of Science, College of Chemical Engineering and Materials Science, Centre of Modern Analytical Technology, Tianjin University of Science and Technology, Tianjin 300457, China
b.
Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education, MOE), Department of Chemistry, Tsinghua University, Beijing 100084 China
c.
Beijing Laviana Pharmatech Co., Ltd., Beijing 102206, China

liuwei2006@tust.edu.cn

chenchao01@mails.tsinghua.edu.cn

Received Date: 4 June 2019
Revised Date: 29 June 2019
Accepted Date: 12 July 2019
Available Online: 12 July 2019

Figures(5)

A range of bench-stable carbazole-containing hypervalent iodine(Ⅲ) reagents were synthesized by I-N bond formation in good yields. This kind of benziodoxolone reagents was used for a C-N coupling reaction to introduce a carbazole group to aromatic heterocycle compounds.
- Carbazoles,
- Hypervalent iodine reagents,
- Benziodoxolones,
- N-ARylation,
- Thiophenes
1. [1]
  (a) A.W. Schmidt, K.R. Reddy, H.J. Knolker, Chem. Rev. 112 (2012) 3193-3328;
  (b) H.J. Knölker, K.R. Reddy, Chem. Rev. 102 (2012) 4303-4427;
  (c) Z. Sadiq, E.A. Hussain, S. Naz, Mini-Rev. Org. Chem. 14 (2017) 469-488;
  (d) J.F. Morin, M. Leclerc, D. Adès, A. Siove, Macromol. Rapid Commun. 26 (2005) 761-778;
  (e) J.V. Grazulevicius, P. Strohriegl, J. Pielichowski, K. Pielichowski, Prog. Polym. Sci. 28 (2003) 1297-1353.
2. [2]
  (a) P. Rajakumar, K. Sekar, V. Shanmugaiah, et al., Eur. J. Med. Chem. 44 (2009) 3040-3045;
  (b) Z. Liu, R.C. Larock, Tetrahedron 63 (2007) 347-355;
  (c) C. Ito, S. Katsuno, M. Itoigawa, et al., J. Nat. Prod. 63 (2000) 125-128.
3. [3]
  (a) M.P. Gaj, C. Fuentes-Hernandez, Y. Zhang, S.R. Marder, B. Kippelen, Org. Electron. 16 (2015) 109-112;
  (b) Z.M. Hudson, Z. Wang, M.G. Helander, Z.H. Lu, S. Wang, Adv. Mater. 24 (2012) 2922-2928;
  (c) L.S. Sapochak, A.B. Padmaperuma, X. Cai, et al., J. Phys. Chem. C 112 (2008) 7989-7996;
  (d) M. Baibarac, M. Lira-Cantú, J. Oró Sol, et al., Compos. Sci. Technol. 67 (2007) 2556-2563.
4. [4]
  (a) I. Tanaka, Y. Tabata, S. Tokito, Chem. Phys. Lett. 400 (2004) 86-89;
  (b) T. Thoms, S. Okada, J.P. Chen, M. Furugori, Thin Solid Films 436 (2003) 264-268.
5. [5]
  (a) M.M. Heravi, Z. Kheilkordi, V. Zadsirjan, M. Heydari, M. Malmir, J. Organoment. Chem. 861 (2018) 17-104;
  (b) P. Ruiz-Castillo, S.L. Buchwald, Chem. Rev. 116 (2016) 12564-12649;
  (c) J. Bariwal, E. Van der Eycken, Chem. Soc. Rev. 42 (2013) 9283-9303.
6. [6]
  (a) D.P. Hari, P. Caramenti, J. Waser, Acc. Chem. Res. 51 (2018) 3212-3225;
  (b) A. Yoshimura, V.V. Zhdankin, Chem. Rev. 116 (2016) 3328-3435;
  (c) Y. Li, D.P. Hari, M.V. Vita, J. Waser, Angew. Chem. Int. Ed. 55 (2016) 4436-4454;
  (d) J. Waser, Synlett. 27 (2016) 2761-2773;
  (e) J.P. Brand, D.F. González, S. Nicolai, J. Waser, Chem. Commun. (Camb.) 47 (2011) 102-115;
  (f) V.V. Zhdankin, Curr. Org. Synth. 2 (2005) 121-145.
7. [7]
  (a) V.V. Zhdankin, A.P. Krasutsky, C.J. Kuehl, et al., J. Am. Chem. Soc. 118 (1996) 5192-5197;
  (b) M.V. Vita, J. Waser, Org. Lett. 15 (2013) 3246-3249;
  (c) A. Sharma, J.F. Hartwig, Nature 517 (2015) 600-604.
8. [8]
  (a) V.V. Zhdankin, M. McSherry, B. Mismash, et al., Tetrahedron Lett. 38 (1997) 21-24;
  (b) X.H. Hu, X.F. Yang, T.P. Loh, ACS Catal. 6 (2016) 5930-5934.
9. [9]
  K. Kiyokawa, T. Kosaka, T. Kojima, S. Minakata, Angew. Chem. Int. Ed. 54 (2015) 13719-13723. doi: 10.1002/anie.201506805
10. [10]
  (a) H. Wang, D. Zhang, H. Sheng, C. Bolm, J. Org. Chem. 82 (2017) 11854-11858;
  (b) H. Wang, D. Zhang, H. Sheng, C. Bolm, Chem. -Eur. J. 24 (2018) 14942-14945.
11. [11]
  (a) P. Caramenti, S. Nicolai, J. Waser, Chem. -Eur. J. 23 (2017) 14702-14706;
  (b) P. Caramenti, R.K. Nandi, J. Waser, Chem. -Eur. J. 24 (2018) 10049-10053.
12. [12]
  (a) S. Cai, C. Chen, Z. Sun, C. Xi, Chem. Commun. (Camb.) 49 (2013) 4552-4554;
  (b) J. Xie, X. Yuan, A. Abdukader, C. Zhu, J. Ma, Org. Lett. 16 (2014) 1768-1771;
  (c) Y. Kuninobu, M. Nishi, M. Kanai, Org. Biomol. Chem. 14 (2016) 8092-8100;
  (d) X. Gao, Y. Geng, S. Han, et al., Org. Lett. 20 (2018) 3732-3735.
1. [1]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
2. [2]
  Yanqi Wu , Yuhong Guan , Peilin Huang , Hui Chen , Liping Bai , Zhihong Jiang . Preparation of norovirus GII loop mediated isothermal amplification freeze-drying microsphere reagents and its application in an on-site integrated rapid detection platform. Chinese Chemical Letters, 2024, 35(9): 109308-. doi: 10.1016/j.cclet.2023.109308
3. [3]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
4. [4]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
5. [5]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
6. [6]
  Yajun Hou , Chuanzheng Zhu , Qiang Wang , Xiaomeng Zhao , Kun Luo , Zongshuai Gong , Zhihao Yuan . ~2.5 nm pores in carbon-based cathode promise better zinc-iodine batteries. Chinese Chemical Letters, 2024, 35(5): 108697-. doi: 10.1016/j.cclet.2023.108697
7. [7]
  Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201
8. [8]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
9. [9]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
10. [10]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
11. [11]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
12. [12]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
13. [13]
  Sanmei Wang , Yong Zhou , Hengxin Fang , Chunyang Nie , Chang Q Sun , Biao Wang . Constant-potential simulation of electrocatalytic N₂ reduction over atomic metal-N-graphene catalysts. Chinese Chemical Letters, 2025, 36(3): 110476-. doi: 10.1016/j.cclet.2024.110476
14. [14]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
15. [15]
  Lijun Mao , Shuo Li , Xin Zhang , Zhan-Ting Li , Da Ma . Cucurbit[n]uril-based nanostructure construction and modification. Chinese Chemical Letters, 2024, 35(8): 109363-. doi: 10.1016/j.cclet.2023.109363
16. [16]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
17. [17]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
18. [18]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
19. [19]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
20. [20]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1016)
HTML views(113)

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