Citation: He Sheng, Qiang Liu, Fei Chen, Zhixiang Wang, Xiangyu Chen. Visible-light-induced N-heterocyclic carbene mediated cascade transformation of N-alkenoxypyridinium salts[J]. Chinese Chemical Letters, ;2022, 33(9): 4298-4302. doi: 10.1016/j.cclet.2022.01.028 shu

Visible-light-induced N-heterocyclic carbene mediated cascade transformation of N-alkenoxypyridinium salts

He Sheng ^a ,
Qiang Liu ^a ,
Fei Chen ^{a, b} ,
Zhixiang Wang ^{a, *,} ,
Xiangyu Chen ^{a, *,}

a.
School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
b.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, China

zxwang@ucas.ac.cn

chenxiangyu20@ucas.ac.cn

Received Date: 20 October 2021
Revised Date: 10 January 2022
Accepted Date: 11 January 2022
Available Online: 18 January 2022

Figures(6)

While N-alkenoxypyridinium salts are widely used for the synthesis of α-functionalized ketones via umpolung strategy, such approaches are usually limited to special nucleophiles at high temperatures. Herein, we developed an alternative photoinduced N-heterocyclic carbene (NHC)- mediated functionalization of N-alkenoxypyridinium salts with various nucleophiles, including tetramethylammonium azide, secondary amines, aryl and alkyl thiols, and even the challenging C(sp³)-nucleophiles, under mild conditions. A cascade radical-radical coupling/nucleophilic substitution sequence was proposed, wherein the NHC enabled the formation of a photoactive electron donor-acceptor complex for α-iodo ketone synthesis.
- N-Heterocyclic carbene,
- N-Alkenoxypyridinium salt,
- α-Functionalized ketones,
- Electron donor-acceptor complex,
- Visible light
1. [1]
  W. Notz, F. Tanaka, C.F. Barbas, Acc. Chem. Res. 37 (2004) 580–591. doi: 10.1021/ar0300468
2. [2]
  S. Mukherjee, J.W. Yang, S. Hoffmann, B. List, Chem. Rev. 107 (2007) 5471–5569. doi: 10.1021/cr0684016
3. [3]
  D. Seebach, Angew. Chem. Int. Ed. 18 (1979) 239–258. doi: 10.1002/anie.197902393
4. [4]
  X. Bugaut, F. Glorius, Chem. Soc. Rev. 41 (2012) 3511–3522. doi: 10.1039/c2cs15333e
5. [5]
  A. Grossmann, D. Enders, Angew. Chem. Int. Ed. 51 (2012) 314–325. doi: 10.1002/anie.201105415
6. [6]
  M.H. Wang, K.A. Scheidt, Angew. Chem. Int. Ed. 55 (2016) 14912–14922. doi: 10.1002/anie.201605319
7. [7]
  D.F. Chen, Z.Y. Han, Y.P. He, J. Yu, L.Z. Gong, Angew. Chem. Int. Ed. 51 (2012) 12307–12310. doi: 10.1002/anie.201205062
8. [8]
  K. Graf, C.L. Rühl, M. Rudolph, F. Rominger, A.S.K. Hashmi, Angew. Chem. Int. Ed. 52 (2013) 12727–12731. doi: 10.1002/anie.201304813
9. [9]
  Z. Xu, H. Chen, Z. Wang, A. Ying, L. Zhang, J. Am. Chem. Soc. 138 (2016) 5515–5518. doi: 10.1021/jacs.6b02533
10. [10]
  Z. Xu, R. Zhai, T. Liang, L. Zhang, Chem. Eur. J. 23 (2017) 14133–14137. doi: 10.1002/chem.201703087
11. [11]
  Q. Liu, C.S. Zhang, H. Sheng, et al., Org. Lett. 22 (2020) 5617–5621. doi: 10.1021/acs.orglett.0c01984
12. [12]
  G.R. Mathi, B. Kweon, Y. Moon, Y. Jeong, S. Hong, Angew. Chem. Int. Ed. 59 (2020) 22675–22683. doi: 10.1002/anie.202010597
13. [13]
  N. Wu, C. Li, J. Mi, Y. Zheng, Z. Xu, Org. Lett. 22 (2020) 7118–7122. doi: 10.1021/acs.orglett.0c02457
14. [14]
  X. Tang, N. Wu, R. Zhai, et al., Org. Biomol. Chem. 17 (2019) 966–972. doi: 10.1039/C8OB02907E
15. [15]
  X. Xia, B. Chen, X. Zeng, B. Xu, Org. Biomol. Chem. 16 (2018) 6918–6922. doi: 10.1039/C8OB02004C
16. [16]
  X. Xia, B. Chen, X. Zeng, B. Xu, Adv. Synth. Catal. 360 (2018) 4429–4434. doi: 10.1002/adsc.201800968
17. [17]
  R.L. Zhai, Y.S. Xue, T. Liang, J.J. Mi, Z. Xu, J. Org. Chem. 83 (2018) 10051–10059. doi: 10.1021/acs.joc.8b01388
18. [18]
  Y. Wen, H. Weimin, D. Xiuqin, L. Xin, S. Jianwei, Angew. Chem. Int. Ed. 55 (2016) 15783–15786. doi: 10.1002/anie.201608371
19. [19]
  L. Su, H. Sun, J. Liu, C. Wang, Org. Lett. 23 (2021) 4662–4666. doi: 10.1021/acs.orglett.1c01400
20. [20]
  H. Ohmiya, ACS Catal. 10 (2020) 6862–6869. doi: 10.1021/acscatal.0c01795
21. [21]
  A. Mavroskoufis, M. Jakob, M.N. Hopkinson, ChemPhotoChem 4 (2020) 5147–5153. doi: 10.1002/cptc.202000120
22. [22]
  Y. Sumida, H. Ohmiya, Chem. Soc. Rev. 50 (2021) 6320–6332. doi: 10.1039/D1CS00262G
23. [23]
  L. Marzo, Eur. J. Org. Chem. 2021 (2021) 4603–4610. doi: 10.1002/ejoc.202100261
24. [24]
  J. Liu, X.N. Xing, J.H. Huang, L.Q. Lu, W.J. Xiao, Chem. Sci. 11 (2020) 10605–10613. doi: 10.1039/D0SC03595E
25. [25]
  K.Q. Chen, H. Sheng, Q. Liu, P.L. Shao, X.Y. Chen, Sci. China Chem. 64 (2021) 7–16. doi: 10.1007/s11426-020-9851-8
26. [26]
  Y.Y. Liu, J. Liu, L.Q. Lu, W.J. Xiao, Top. Curr. Chem. 377 (2019) 37. doi: 10.1007/s41061-019-0265-0
27. [27]
  T. Ishii, K. Nagao, H. Ohmiya, Chem. Sci. 11 (2020) 5630–5636. doi: 10.1039/D0SC01538E
28. [28]
  L. Dai, S. Ye, Chin. Chem. Lett. 32 (2021) 660–667. doi: 10.1016/j.cclet.2020.08.027
29. [29]
  K.Q. Chen, Z.X. Wang, X.Y. Chen, Org. Lett. 22 (2020) 8059–8064. doi: 10.1021/acs.orglett.0c03006
30. [30]
  D.A. DiRocco, T. Rovis, J. Am. Chem. Soc. 134 (2012) 8094–8097. doi: 10.1021/ja3030164
31. [31]
  Z.H. Gao, Z.H. Xia, L. Dai, S. Ye, Adv. Synth. Catal. 362 (2020) 1819–1824. doi: 10.1002/adsc.202000164
32. [32]
  Z.H. Xia, L. Dai, Z.H. Gao, S. Ye, Chem. Commun. 56 (2020) 1525–1528. doi: 10.1039/C9CC09272B
33. [33]
  L. Dai, Z.H. Xia, Y.Y. Gao, Z.H. Gao, S. Ye, Angew. Chem. Int. Ed. 58 (2019) 18124–18130. doi: 10.1002/anie.201909017
34. [34]
  L. Dai, S. Ye, Org. Lett. 22 (2020) 986–990. doi: 10.1021/acs.orglett.9b04533
35. [35]
  A.V. Bay, K.P. Fitzpatrick, R.C. Betori, K.A. Scheidt, Angew. Chem. Int. Ed. 59 (2020) 9143–9148. doi: 10.1002/anie.202001824
36. [36]
  A.V. Bay, K.P. Fitzpatrick, G.A. González-Montiel, et al., Angew. Chem. Int. Ed. 60 (2021) 17925–17931. doi: 10.1002/anie.202105354
37. [37]
  Q.Y. Meng, N. Döben, A. Studer, Angew. Chem. Int. Ed. 59 (2020) 19956–19960. doi: 10.1002/anie.202008040
38. [38]
  Q.Y. Meng, L. Lezius, A. Studer, Nat. Commun. 12 (2021) 2068. doi: 10.1038/s41467-021-22292-z
39. [39]
  K. Liu, A. Studer, J. Am. Chem. Soc. 143 (2021) 4903–4909. doi: 10.1021/jacs.1c01022
40. [40]
  S.C. Ren, W.X. Lv, X. Yang, et al., ACS Catal. 11 (2021) 2925–2934. doi: 10.1021/acscatal.1c00165
41. [41]
  H. Sheng, Q. Liu, X.D. Su, et al., Org. Lett. 22 (2020) 7187–7192. doi: 10.1021/acs.orglett.0c02523
42. [42]
  K.Q. Chen, J. Shen, Z.X. Wang, X.Y. Chen, Chem. Sci. 12 (2021) 6684–6690. doi: 10.1039/D1SC01024G
43. [43]
  Q. Liu, Y. Lu, H. Sheng, et al., Angew. Chem. Int. Ed. 60 (2021) 25477–25484. doi: 10.1002/anie.202111006
44. [44]
  Q. Liu, X.Y. Chen, Org. Chem. Front. 7 (2020) 2082–2087. doi: 10.1039/D0QO00494D
45. [45]
  T. Patonay, K. Kónya, É. Juhász-Tóth, Chem. Soc. Rev. 40 (2011) 2797–2847. doi: 10.1039/c0cs00101e
46. [46]
  S. Faiz, A.F. Zahoor, N. Rasool, et al., Molecules 20 (2015) 14699–14745. doi: 10.3390/molecules200814699
47. [47]
  M.P. DeMartino, K. Chen, P.S. Baran, J. Am. Chem. Soc. 130 (2008) 11546–11560. doi: 10.1021/ja804159y
48. [48]
  T. Fujisawa, K. Igeta, S. Odake, et al., Bioorg. Med. Chem. 10 (2002) 2569–2581. doi: 10.1016/S0968-0896(02)00109-8
49. [49]
  M. Whittaker, C.D. Floyd, P. Brown, A.J.H. Gearing, Chem. Rev. 99 (1999) 2735–2776. doi: 10.1021/cr9804543
1. [1]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
2. [2]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
3. [3]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
4. [4]
  Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
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]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
7. [7]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
8. [8]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2023.100463
9. [9]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
10. [10]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
11. [11]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
12. [12]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
13. [13]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
14. [14]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
15. [15]
  Xin Wang , Changzhao Chen , Qishen Wang , Kai Dai . Graphene quantum dot modified Bi2MoO6 nanoflower for efficient degradation of BPA under visible light. Chinese Journal of Structural Chemistry, 2024, 43(12): 100473-100473. doi: 10.1016/j.cjsc.2024.100473
16. [16]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
17. [17]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
18. [18]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
19. [19]
  Yuting Wu , Haifeng Lv , Xiaojun Wu . Design of two-dimensional porous covalent organic framework semiconductors for visible-light-driven overall water splitting: A theoretical perspective. Chinese Journal of Structural Chemistry, 2024, 43(11): 100375-100375. doi: 10.1016/j.cjsc.2024.100375
20. [20]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(571)
HTML views(44)

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