journal article·2024-10Open access

Photoinduced Single Electron Reduction of the 4‐O‐5 Linkage in Lignin Models for C‐P Coupling Catalyzed by Bifunctional N‐Heterocyclic Carbenes

Qiang Liu, Ying‐Zheng Ren, Bei‐Bei Zhang, Wen‐Xin Tang, Zhi‐Xiang Wang, Lin He, Xiang‐Yu Chen

Advanced Science· Volume 11· Issue 38

Abstract

Abstract Catalytic activation of Caryl‐O bonds is considered as a powerful strategy for the production of aromatics from lignin. However, due to the high reduction potentials of diaryl ether 4‐O‐5 linkage models, their single electron reduction remains a daunting challenge. This study presents the blue light‐induced bifunctional N‐heterocyclic carbene (NHC)‐catalyzed one‐electron reduction of diaryl ether 4‐O‐5 linkage models for the synthesis of trivalent phosphines. The H‐bond between the newly devised bifunctional NHC and diaryl ethers is responsible for the success of the single electron transfer. Furthermore, this approach demonstrates selective one‐electron reduction of unsymmetric diaryl ethers, oligomeric phenylene oxide, and lignin model.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Radical Photochemical Reactions · Catalytic C–H Functionalization Methods · Sulfur-Based Synthesis Techniques

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

School of Chemical Sciences University of the Chinese Academy of Sciences Beijing National Laboratory for Molecular Sciences Beijing 100049 China

State Key Laboratory Incubation Base for Green Processing of Chemical Engineering School of Chemistry and Chemical Engineering Shihezi University Xinjiang 832000 China

Binzhou Institute of Technology Weiqiao‐UCAS Science and Technology Park Binzhou Shandong 256606 China

Funding

National Natural Science Foundation of China · Beijing National Laboratory for Molecular Sciences

References (75)

Show source-provided references
1. 10.1002/anie.20080147610.1002/anie.200801476 ↗
2. 10.1038/474S012a10.1038/474S012a ↗
3. 10.1039/C7CS00566K10.1039/C7CS00566K ↗
4. 10.1021/jz201201q10.1021/jz201201q ↗
5. 10.1016/j.cplett.2012.07.01710.1016/j.cplett.2012.07.017 ↗
6. 10.1021/acs.chemrev.5b0015510.1021/acs.chemrev.5b00155 ↗
7. 10.1021/acs.chemrev.0c0008810.1021/acs.chemrev.0c00088 ↗
8. 10.1126/science.120043710.1126/science.1200437 ↗
9. 10.1021/ja308591210.1021/ja3085912 ↗
10. 10.1039/c3sc22256j10.1039/c3sc22256j ↗
11. 10.1002/anie.20150913310.1002/anie.201509133 ↗
12. 10.1021/acscatal.5b0208910.1021/acscatal.5b02089 ↗
13. 10.1021/jacs.7b1053710.1021/jacs.7b10537 ↗
14. 10.1002/anie.20130534210.1002/anie.201305342 ↗
15. 10.1021/acs.accounts.5b0005110.1021/acs.accounts.5b00051 ↗
16. 10.1002/anie.20221195210.1002/anie.202211952 ↗
17. 10.1021/ef00029a02810.1021/ef00029a028 ↗
18. 10.1021/cr068360d10.1021/cr068360d ↗
19. 10.1002/cctc.20100018110.1002/cctc.201000181 ↗
20. 10.1021/ja309915e10.1021/ja309915e ↗
21. 10.1039/C4CY01417K10.1039/C4CY01417K ↗
22. 10.1002/anie.20161107610.1002/anie.201611076 ↗
23. 10.1038/s41467-020-19944-x10.1038/s41467-020-19944-x ↗
24. 10.1021/acscatal.3c0230110.1021/acscatal.3c02301 ↗
25. 10.1021/jacsau.1c0016810.1021/jacsau.1c00168 ↗
26. 10.1021/acscatal.8b0221410.1021/acscatal.8b02214 ↗
27. 10.1002/anie.20171221110.1002/anie.201712211 ↗
28. 10.1038/s41929-020-0495-010.1038/s41929-020-0495-0 ↗
29. 10.1021/ar00155a00510.1021/ar00155a005 ↗
30. 10.1021/cr300503r10.1021/cr300503r ↗
31. 10.1021/cr400689s10.1021/cr400689s ↗
32. 10.1021/acs.chemrev.6b0005710.1021/acs.chemrev.6b00057 ↗
33. 10.1021/acs.chemrev.6b0001810.1021/acs.chemrev.6b00018 ↗
34. 10.1002/anie.20170976610.1002/anie.201709766 ↗
35. 10.1039/C8CS00054A10.1039/C8CS00054A ↗
36. 10.1002/anie.20180310210.1002/anie.201803102 ↗
37. 10.1016/j.cclet.2022.06.04810.1016/j.cclet.2022.06.048 ↗
38. 10.1021/acs.orglett.4c0043310.1021/acs.orglett.4c00433 ↗
39. Ghosh I. · Phys. Sci. Rev. · 2019 · 4
40. 10.1002/anie.20191576210.1002/anie.201915762 ↗
41. 10.1038/s41929-020-00515-810.1038/s41929-020-00515-8 ↗
42. 10.1021/acscentsci.0c0054910.1021/acscentsci.0c00549 ↗
43. 10.1002/anie.20200928810.1002/anie.202009288 ↗
44. 10.1021/acs.chemrev.1c0055810.1021/acs.chemrev.1c00558 ↗
45. 10.1021/jacs.2c0323510.1021/jacs.2c03235 ↗
46. 10.1007/s11426-023-1787-310.1007/s11426-023-1787-3 ↗
47. 10.1126/science.125823210.1126/science.1258232 ↗
48. 10.1021/ja500031m10.1021/ja500031m ↗
49. 10.1039/C5SC03013G10.1039/C5SC03013G ↗
50. 10.1021/jacs.5b1345010.1021/jacs.5b13450 ↗
51. 10.1002/anie.20170300410.1002/anie.201703004 ↗
52. 10.1002/anie.20171169210.1002/anie.201711692 ↗
53. 10.1021/jacs.8b1222310.1021/jacs.8b12223 ↗
54. 10.1021/jacs.0c0589910.1021/jacs.0c05899 ↗
55. 10.1021/jacs.9b1232810.1021/jacs.9b12328 ↗
56. 10.1038/s41929-019-0369-510.1038/s41929-019-0369-5 ↗
57. 10.1021/jacs.9b1067810.1021/jacs.9b10678 ↗
58. 10.1038/s41586-020-2131-110.1038/s41586-020-2131-1 ↗
59. 10.1126/science.aba241910.1126/science.aba2419 ↗
60. 10.1002/anie.20210716910.1002/anie.202107169 ↗
61. 10.1021/jacs.1c0598810.1021/jacs.1c05988 ↗
62. 10.1021/jacs.1c0599410.1021/jacs.1c05994 ↗
63. 10.1126/science.abq866310.1126/science.abq8663 ↗
64. 10.1021/jacs.3c0578710.1021/jacs.3c05787 ↗
65. 10.1016/j.chempr.2021.04.01610.1016/j.chempr.2021.04.016 ↗
66. 10.1002/anie.20221846810.1002/anie.202218468 ↗
67. 10.1021/acs.accounts.9b0063510.1021/acs.accounts.9b00635 ↗
68. 10.1021/ja108082210.1021/ja1080822 ↗
69. 10.1021/cr400274j10.1021/cr400274j ↗
70. 10.1021/jacs.6b0382310.1021/jacs.6b03823 ↗
71. 10.1021/jacs.8b0608910.1021/jacs.8b06089 ↗
72. 10.1007/s11426-019-9611-x10.1007/s11426-019-9611-x ↗
73. 10.1021/ja058783h10.1021/ja058783h ↗
74. 10.1021/acscatal.9b0336610.1021/acscatal.9b03366 ↗
75. 10.1002/anie.20231076410.1002/anie.202310764 ↗