Citation: Le Jia, Chao-Jun Li, Huiying Zeng. Cleavage∕cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C–O bond cleavage[J]. Chinese Chemical Letters, ;2022, 33(3): 1519-1523. doi: 10.1016/j.cclet.2021.08.125 shu

Cleavage∕cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C–O bond cleavage

Le Jia ^a ,
Chao-Jun Li ^b ,
Huiying Zeng ^{a, *,}

a.
The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
b.
Department of Chemistry, FQRNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, Quebec H3A 0B8, Canada

zenghy@lzu.edu.cn

Received Date: 4 August 2021
Revised Date: 28 August 2021
Accepted Date: 30 August 2021
Available Online: 6 September 2021

Figures(3)

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and commercial chemicals. Up to now, the selective cleavage of C–O linkages of lignin to afford chemicals contains only C, H and O atoms. Our group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds. Herein, we present a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C–O bond cleavage for the preparation of benzyl amine compounds and phenols.
- β-O-4 Linkage,
- Lignin,
- C-O bond cleavage,
- Cross-coupling reaction,
- Palladium-catalyzed
1. [1]
  A.J. Ragauskas, C.K. Williams, B.H. Davison, et al., Science 311 (2006) 484-489. doi: 10.1126/science.1114736
2. [2]
  G.W. Huber, S. Iborra, A. Corma, Chem. Rev. 106 (2006) 4044-4098. doi: 10.1021/cr068360d
3. [3]
  J. Ohlrogge, D. Allen, B. Berguson, et al., Science 324 (2009) 1019-1020. doi: 10.1126/science.1171740
4. [4]
  Y. Kim, C.J. Li, Green Synth. Catal. 1 (2020) 1-11. doi: 10.1016/j.gresc.2020.06.002
5. [5]
  Y.C. Shao, Y. Ding, J.H. Dai, et al., Green Synth. Catal. 2 (2021) 187-197. doi: 10.1016/j.gresc.2021.01.006
6. [6]
  P. McKendry, Bioresource Technology 83 (2002) 37-46. doi: 10.1016/S0960-8524(01)00118-3
7. [7]
  J.R. Regalbuto, Science 325 (2009) 822-824. doi: 10.1126/science.1174581
8. [8]
  J. Ralph, K. Lundquis, G. Brunow, et al., Phytochem. Rev. 3 (2004) 29-60. doi: 10.1023/B:PHYT.0000047809.65444.a4
9. [9]
  J. Zakzeski, P.C.A. Bruijnincx, A.L. Jongerius, et al., Chem. Rev. 110 (2010) 3552-3599. doi: 10.1021/cr900354u
10. [10]
  S. Gillet, M. Aguedo, L. Petitjean, et al., Green Chem. 19 (2017) 4200-4233. doi: 10.1039/C7GC01479A
11. [11]
  Y.X. Jing, L. Dong, Y. Guo, et al., ChemSusChem 13 (2020) 4181-4198. doi: 10.1002/cssc.201903174
12. [12]
  J.M. Nichols, L.M. Bishop, R.G. Bergman, et al., J. Am. Chem. Soc. 132 (2010) 12554-12555. doi: 10.1021/ja106101f
13. [13]
  W. Lan, M.T. Amiri, C.M. Hunston, Angew. Chem. Int. Ed. 57 (2018) 1356-1360. doi: 10.1002/anie.201710838
14. [14]
  J. Mottweiler, T. Rinesch, C. Besson, et al., Green Chem. 17 (2015) 5001-5008. doi: 10.1039/C5GC01306B
15. [15]
  M.V. Galkin, S. Sawadjoon, V. Rohde, ChemCatChem 6 (2014) 179-184. doi: 10.1002/cctc.201300540
16. [16]
  Y.X. Liu, C.Z. Li, W. Miao, et al., ACS Catal. 9 (2019) 4441-4447. doi: 10.1021/acscatal.9b00669
17. [17]
  S.K. Hanson, R.T. Baker, J.C. Gordon, et al., Inorg. Chem. 49 (2010) 5611-5618. doi: 10.1021/ic100528n
18. [18]
  T.W. Lee, J.W. Yang, Green Chem. 20 (2018) 3761-3771. doi: 10.1039/C8GC01886C
19. [19]
  T.V. Stein, T.D. Hartog, J. Buendia, Angew. Chem. Int. Ed. 54 (2015) 5859-5863. doi: 10.1002/anie.201410620
20. [20]
  S. Dabral, J.G. Hernández, P.C.J. Kamer, ChemSusChem 10 (2017) 2707-2713. doi: 10.1002/cssc.201700703
21. [21]
  Y.L. Wang, J.H. He, Y. T Zhang, CCS Chem. 2 (2020) 107-117. doi: 10.31635/ccschem.020.201900076
22. [22]
  X.X. Li, B. Zhang, X.L. Pan, et al., ChemSusChem 13 (2020) 4409-4419. doi: 10.1002/cssc.201903286
23. [23]
  Y. Shao, Q.N. Xia, L. Dong, et al., Nat. Commun. 8 (2017) 16104-16113. doi: 10.1038/ncomms16104
24. [24]
  H.W. Guo, B. Zhang, C. Z Li, et al., ChemSusChem 9 (2016) 3220-3229. doi: 10.1002/cssc.201600901
25. [25]
  S.K. Hanson, R. L Wu, L.A. "Pete" Silks, Angew. Chem. Int. Ed. 51 (2012) 3410-3413. doi: 10.1002/anie.201107020
26. [26]
  V. Froidevaux, C. Negrell, S. Caillol, et al., Chem. Rev. 116 (2016) 14181-14224. doi: 10.1021/acs.chemrev.6b00486
27. [27]
  P.R. Castillo, S.L. Buchwald, Chem. Rev. 116 (2016) 12564-12649. doi: 10.1021/acs.chemrev.6b00512
28. [28]
  T. Irrgang, R. Kempe, Chem. Rev. 119 (2019) 2524-2549. doi: 10.1021/acs.chemrev.8b00306
29. [29]
  S. Song, V.F.K. Yuen, L. Di, et al., Angew. Chem. Int. Ed. 59 (2020) 19846-19850. doi: 10.1002/anie.202006315
30. [30]
  H. Zeng, D.W. Cao, Z.H. Qiu, et al., Angew. Chem. Int. Ed. 57 (2018) 3752-3757. doi: 10.1002/anie.201712211
31. [31]
  D. Cao, H. Zeng, C.J. Li, ACS Catal. 8 (2018) 8873-8878. doi: 10.1021/acscatal.8b02214
32. [32]
  D. Cao, J. Yu, H. Zeng, et al., J. Agric. Food Chem. 68 (2020) 13200-13205. doi: 10.1021/acs.jafc.0c00644
33. [33]
  Y. Lang, C.J. Li, H. Zeng, Synlett 32 (2021) 429-435. doi: 10.1504/ijise.2021.119710
34. [34]
  Z. Qiu, H. Zeng, C.J. Li, Acc. Chem. Res. 53 (2020) 2395-2413. doi: 10.1021/acs.accounts.0c00479
35. [35]
  H. Zeng, J. Yu, C.J. Li, Chem. Commun. 56 (2020) 1239-1242. doi: 10.1039/C9CC09347H
36. [36]
  Z. Wang, J. Niu, H. Zeng, et al., Org. Lett. 21 (2019) 7033-7037. doi: 10.1021/acs.orglett.9b02613
37. [37]
  H. Zeng, Z. Qiu, A. Dominguez-Huerta, et al., ACS Catal. 7 (2017) 510-519. doi: 10.1021/acscatal.6b02964
38. [38]
  Q. Dou, C.J. Li, H. Zeng, Chem. Sci. 11 (2020) 5740-5744. doi: 10.1039/D0SC01585G
39. [39]
  Q. Dou, L. Geng, B. Cheng, et al., Chem. Commun. 57 (2021) 8429-8432. doi: 10.1039/D1CC03496K
40. [40]
  Z. Chen, H. Zeng, S.A. Girard, et al., Angew. Chem. Int. Ed. 54 (2015) 14487-14491. doi: 10.1002/anie.201506751
41. [41]
  Z. Chen, H. Zeng, H. Gong, et al., Chem. Sci. 6 (2015) 4174-4178. doi: 10.1039/C5SC00941C
42. [42]
  J. Yu, C.J. Li, H. Zeng, Angew. Chem. Int. Ed. 60 (2021) 4043-4048. doi: 10.1002/anie.202010845
43. [43]
  H. Zeng, C.J. Li, Conversion of lignin into high value chemical products, in: R.A. Meyers (Ed.), Encyclopedia of Sustainability Science and Technology, Springer Nature, New York, 2018, pp. 1-20.
44. [44]
  Q. Mei, X. Shen, H. Liu, et al., Chin. Chem. Lett. 30 (2019) 15-24. doi: 10.1016/j.cclet.2018.04.032
45. [45]
  X.P. Ouyang, Y. Yang, G.D. Zhu, et al., Chin. Chem. Lett. 26 (2015) 980-982. doi: 10.1016/j.cclet.2015.05.011
46. [46]
  X.P. Ouyang, C.L. Liu, Y.X. Pang, et al., Chin. Chem. Lett. 24 (2013) 1091-1094. doi: 10.1016/j.cclet.2013.09.001
47. [47]
  C.Z. Li, X.C. Zhao, A.Q. Wang, et al., Chem. Rev. 115 (2015) 11559-11624. doi: 10.1021/acs.chemrev.5b00155
48. [48]
  C.Z. Li, B. Zhang, Y.X. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 20666-20671.
1. [1]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
2. [2]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
3. [3]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
4. [4]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
5. [5]
  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
6. [6]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
7. [7]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
8. [8]
  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
9. [9]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
10. [10]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
11. [11]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
12. [12]
  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
13. [13]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
14. [14]
  Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C₃N₄/O-doped-C₃N₅ for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
15. [15]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
16. [16]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
17. [17]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
18. [18]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
19. [19]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
20. [20]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(709)
HTML views(122)

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