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DOI: 10.1055/a-2705-8764
Heterobenzylic C(sp3)─H Acylation of Isoindolinones via Photoinduced Intermolecular Hydrogen Atom Transfer Strategy
Autoren
Funding Information The Department of Science and Technology-SERB, India (CRG/2021/001143) and the Seed grant-SG20210167, Vellore Institute of Technology, Vellore.
Gefördert durch: Vellore Institute of Techmology SG20210167
Gefördert durch: Council of Scientific and Industrial Research (CSIR), New Delhi, India 09/0844(18215)/2024-EMR-I
Abstract
Heterobenzylic C(sp3)−H functionalization of isoindolinones remains challenging yet highly desirable. Herein, we present a photo-induced hydrogen atom transfer (HAT) strategy for heterobenzylic C(sp3)−H acylation of isoindolinones using acyl azolium salts under mild reaction conditions. This metal-free protocol offers excellent functional group compatibility and avoids the usage of Lewis acids or oxidants, providing a sustainable and efficient approach to C–H acylation.
Publikationsverlauf
Eingereicht: 12. Juni 2025
Angenommen nach Revision: 28. August 2025
Accepted Manuscript online:
19. September 2025
Artikel online veröffentlicht:
24. Oktober 2025
© 2025. Thieme. All rights reserved.
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References
- 1 Sartori G, Maggi R. Chem Rev 2006; 106: 1077
- 2 Kumar V, Turnbull WB, Kumar A. ACS Catal 2022; 12: 10742
- 3 Ohata J. Org Biomol Chem 2024; 22: 3544
- 4 Grover J, Sebastian AT, Maiti S, Bissember AC, Maiti D. Chem Soc Rev 2006; 2025: 54
- 5 Hu J, Pradhan S, Waiba S, Das S. Chem Sci 2025; 16: 1041
- 6 Capaldo L, Ravelli D, Fagnoni M. Chem Rev 1875; 2022: 122
- 7 Cao J, Zhu JL, Scheidt KA. Chem Sci 2024; 15: 154
- 8 Meng Q-Y, Lezius L, Studer A. Nat Commun 2021; 12: 2068
- 9 Bailly C. Eur J Med Chem Rep 2023; 9: 100112
- 10 Kaur Bhatia R. Curr Top Med Chem 2017; 17: 189
- 11 Upadhyay SP, Thapa P, Sharma R, Sharma M. Fitoterapia 2020; 146: 104722
- 12 Chen L, Zou Y-X. Adv Synth Catal 2021; 363: 4159
- 13 Savela R, Méndez-Gálvez C. Chem Eur J 2021; 27: 5344
- 14 Samanta S, Ali SA, Bera A, Giri S, Samanta K. New J Chem 2022; 46: 7780
- 15 Yuan Y-C, Bruneau C, Roisnel T, Gramage-Doria R. Catal Sci Technol 2019; 9: 4711
- 16 Yuan Y-C, Goujon M, Bruneau C, Roisnel T, Gramage-Doria R. J Org Chem 2019; 84: 16183
- 17 Yuan Y-C, Bruneau C, Roisnel T, Gramage-Doria R. J Org Chem 2019; 84: 12893
- 18 Chang Z, Huang J, Wang S. et al. Nat Commun 2021; 12: 4342
- 19 Sreedharan R, Gandhi T. J Org Chem 2023; 88: 8480
- 20 Jiménez J, Kim B, Walsh PJ. Adv Synth Catal 2016; 358: 2829
- 21 Maity B, Dutta S, Cavallo L. Chem Soc Rev 2023; 52: 5373
- 22 Chai Z. Angew Chem 2024; 136: e202316444
- 23 Tu J-L, Zhu Y, Li P, Huang B. Org Chem Front 2024; 11: 5278
- 24 Galeotti M, Salamone M, Bietti M. Chem Soc Rev 2022; 51: 2171
- 25 Mavroskoufis A, Rajes K, Golz P. et al. Angew Chem Int Ed 2020; 59: 3190
- 26 Rourke MJ, Wang CT, Schull CR, Scheidt KA. ACS Catal 2023; 13: 7987
- 27 Zhu JL, Schull CR, Tam AT. et al. J Am Chem Soc 2023; 145: 1535
- 28 Sivaraj C, Maiti D, Gandhi T. Chem Eur J 2024; 30: e202303626