Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives
Source abstract
Abstract
Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, a visible light‐induced three‐component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex bioactive molecules. This method offers a promising alternative route for modular synthesis of peptide‐derived bio‐relevant compounds
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
National and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. China
State Key Laboratory of Natural Medicines Department of Organic Chemistry China Pharmaceutical University Nanjing 210009 P. R. China
Jiangsu Engineering Research Center of Interfacial Chemistry Nanjing University Nanjing 210023 P. R. China
Funding
National Natural Science Foundation of China
References (100+)
Show source-provided references
1. 10.1016/j.drudis.2014.10.00310.1016/j.drudis.2014.10.003 ↗
2. 10.1021/acs.jmedchem.7b0031810.1021/acs.jmedchem.7b00318 ↗
3. 10.1038/s41573-020-00135-810.1038/s41573-020-00135-8 ↗
4. 10.2174/13816121079329255510.2174/138161210793292555 ↗
5. 10.1021/acs.chemrev.9b0000810.1021/acs.chemrev.9b00008 ↗
6. 10.1016/j.cbpa.2008.03.00910.1016/j.cbpa.2008.03.009 ↗
7. 10.2174/13816121079329243810.2174/138161210793292438 ↗
8. a)Q.Wang J.Guan J.Wan Z.Li R. S. C.Adv 2020 10 24397;10.1039/D0RA04155F ↗
9. 10.1002/pat.478910.1002/pat.4789 ↗
10. 10.1021/ja207463b10.1021/ja207463b ↗
11. 10.1039/D0CS00556H10.1039/D0CS00556H ↗
12. 10.1016/j.apsb.2022.07.02010.1016/j.apsb.2022.07.020 ↗
13. 10.1016/j.biomaterials.2021.12113910.1016/j.biomaterials.2021.121139 ↗
14. 10.1016/j.ejmech.2020.11278110.1016/j.ejmech.2020.112781 ↗
15. 10.1126/science.aam734010.1126/science.aam7340 ↗
16. 10.1038/s41392-022-00999-910.1038/s41392-022-00999-9 ↗
17. 10.1038/nature1352710.1038/nature13527 ↗
18. 10.1021/acsmedchemlett.1c0017810.1021/acsmedchemlett.1c00178 ↗
19. 10.1002/ejoc.20180089610.1002/ejoc.201800896 ↗
20. 10.1021/jacs.4c0594910.1021/jacs.4c05949 ↗
21. 10.1021/acs.accounts.3c0026010.1021/acs.accounts.3c00260 ↗
22. 10.1021/jacs.4c0002310.1021/jacs.4c00023 ↗
23. 10.1039/D3SC02543H10.1039/D3SC02543H ↗
24. 10.1021/jacs.3c0384010.1021/jacs.3c03840 ↗
25. 10.1039/D0CC08126D10.1039/D0CC08126D ↗
26. 10.1021/acscatal.3c0407510.1021/acscatal.3c04075 ↗
27. 10.1021/acscatal.3c0497410.1021/acscatal.3c04974 ↗
28. 10.1021/acs.orglett.2c0295110.1021/acs.orglett.2c02951 ↗
29. 10.1038/s41467-022-35249-710.1038/s41467-022-35249-7 ↗
30. 10.1039/C9QO01175G10.1039/C9QO01175G ↗
31. 10.1002/cssc.20180221610.1002/cssc.201802216 ↗
32. 10.1002/anie.20180940010.1002/anie.201809400 ↗
33. 10.1002/anie.20191455510.1002/anie.201914555 ↗
34. 10.1038/s41467-019-12722-410.1038/s41467-019-12722-4 ↗
35. 10.1039/D2SC04507A10.1039/D2SC04507A ↗
36. 10.1007/s11426-019-9652-x10.1007/s11426-019-9652-x ↗
37. 10.1021/jacs.1c0628110.1021/jacs.1c06281 ↗
38. 10.1021/acs.orglett.3c0058210.1021/acs.orglett.3c00582 ↗
39. 10.1002/anie.20191421510.1002/anie.201914215 ↗
40. 10.1021/jacs.9b0732310.1021/jacs.9b07323 ↗
41. 10.1002/anie.20190871810.1002/anie.201908718 ↗
42. 10.1002/adsc.20200022010.1002/adsc.202000220 ↗
43. 10.1021/acs.orglett.4c0234810.1021/acs.orglett.4c02348 ↗
44. 10.1021/jacs.1c1078310.1021/jacs.1c10783 ↗
45. 10.1039/D0CC00641F10.1039/D0CC00641F ↗
46. 10.1002/anie.20190667210.1002/anie.201906672 ↗
47. 10.1039/D3SC02402D10.1039/D3SC02402D ↗
48. 10.1021/jacs.1c0345910.1021/jacs.1c03459 ↗
49. 10.1021/acs.orglett.1c0190410.1021/acs.orglett.1c01904 ↗
50. 10.1038/s41929-019-0415-310.1038/s41929-019-0415-3 ↗
51. 10.1038/s41557-022-01092-y10.1038/s41557-022-01092-y ↗
52. 10.1002/anie.20230676410.1002/anie.202306764 ↗
53. 10.1002/chem.20220396610.1002/chem.202203966 ↗
54. 10.1002/anie.20191238310.1002/anie.201912383 ↗
55. 10.1021/jacs.3c0261110.1021/jacs.3c02611 ↗
56. 10.1002/anie.20220270610.1002/anie.202202706 ↗
57. 10.1021/acs.orglett.2c0395610.1021/acs.orglett.2c03956 ↗
58. 10.1002/cjoc.20230018810.1002/cjoc.202300188 ↗
59. 10.1016/j.checat.2022.03.00710.1016/j.checat.2022.03.007 ↗
60. 10.1021/acs.orglett.0c0245810.1021/acs.orglett.0c02458 ↗
61. 10.1039/D2QO00768A10.1039/D2QO00768A ↗
62. 10.1021/acs.orglett.1c0322910.1021/acs.orglett.1c03229 ↗
63. 10.1002/anie.20240049410.1002/anie.202400494 ↗
64. 10.1021/acs.orglett.3c0418310.1021/acs.orglett.3c04183 ↗
65. 10.1038/s44160-023-00277-810.1038/s44160-023-00277-8 ↗
66. 10.1039/D2QO01699K10.1039/D2QO01699K ↗
67. 10.1002/anie.20220988210.1002/anie.202209882 ↗
68. 10.1021/jacs.3c0401610.1021/jacs.3c04016 ↗
69. 10.1002/anie.20231097810.1002/anie.202310978 ↗
70. 10.1038/s41557-024-01560-710.1038/s41557-024-01560-7 ↗
71. 10.1016/S0065-3160(08)60045-310.1016/S0065-3160(08)60045-3 ↗
72. 10.1002/advs.20240242810.1002/advs.202402428 ↗
73. 10.1021/acscatal.2c0108710.1021/acscatal.2c01087 ↗
74. 10.1038/s41573-023-00703-810.1038/s41573-023-00703-8 ↗
75. 10.4155/bio-2017-013710.4155/bio-2017-0137 ↗
76. 10.1038/nature1128610.1038/nature11286 ↗
77. 10.4103/1008-682X.12913310.4103/1008-682X.129133 ↗
78. 10.1021/acs.orglett.2c0300810.1021/acs.orglett.2c03008 ↗
79. 10.1016/j.cclet.2023.10840310.1016/j.cclet.2023.108403 ↗
80. 10.1002/anie.20230310410.1002/anie.202303104 ↗
81. 10.1055/a-2114-882310.1055/a-2114-8823 ↗
82. 10.1039/D2SC01241C10.1039/D2SC01241C ↗
83. 10.1002/anie.20190372610.1002/anie.201903726 ↗
84. 10.1021/acs.joc.8b0094610.1021/acs.joc.8b00946 ↗
85. 10.1039/C4OB00234B10.1039/C4OB00234B ↗
86. 10.1002/anie.20221297510.1002/anie.202212975 ↗
87. 10.1021/jacs.2c1300710.1021/jacs.2c13007 ↗
88. 10.1021/acs.orglett.2c0233010.1021/acs.orglett.2c02330 ↗
89. 10.1021/acscatal.2c0637710.1021/acscatal.2c06377 ↗
90. 10.1021/acs.orglett.8b0271810.1021/acs.orglett.8b02718 ↗
91. 10.1038/s41929-022-00841-z10.1038/s41929-022-00841-z ↗
92. 10.1021/acscatal.3c0066910.1021/acscatal.3c00669 ↗
93. 10.1021/jacs.8b0893310.1021/jacs.8b08933 ↗
94. 10.1021/acscatal.0c0215910.1021/acscatal.0c02159 ↗
95. 10.3762/bjoc.14.17910.3762/bjoc.14.179 ↗
96. 10.1002/adsc.20130075110.1002/adsc.201300751 ↗
97. 10.1021/cr300503r10.1021/cr300503r ↗
98. 10.1038/s41557-023-01258-210.1038/s41557-023-01258-2 ↗
99. 10.1002/anie.20180310210.1002/anie.201803102 ↗
100. 10.1021/acs.joc.6b0124010.1021/acs.joc.6b01240 ↗