The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

Scholarly Works

• Dai, C.; Huang, C.; Ye, M.; Liu, J.; Cheng, H. Mild Catalyst- and Additive-Free Three-Component Synthesis of 3-Thioisoindolinones and Tricyclic γ-Lactams Accelerated by Microdroplet Chemistry. The Journal of organic chemistry 2024, 89, 14818–14830. doi:10.1021/acs.joc.4c01568
• Karu, S. K.; Malapaka, C.; Veludandi, M. An Acid-Mediated Multicomponent Domino Reaction for the Synthesis of N-Substituted Isoindolinones. Synthesis 2024. doi:10.1055/a-2380-9676
• Kemp, A.; Durand, M.; Wall, D.; Szieber, P.; Hermanns, M. I.; Oelgemöller, M. Synthesis of 1H-isoindolin-1-ones via a simple photodecarboxylative addition of carboxylates to phthalimides and evaluation of their antibiotic activity. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 2024, 23, 1353–1360. doi:10.1007/s43630-024-00600-y
• Feng, S.; Liu, H.; Li, Y.; Fang, Y. Photoredox-catalyzed radical-radical cross coupling of ketyl radicals with unstabilized primary alkyl radicals. Chemical communications (Cambridge, England) 2024, 60, 4431–4434. doi:10.1039/d4cc00620h
• Lan, C. B.; Auclair, K. 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400071
• Gupta, M. K.; Panda, A.; Panda, S.; Sharma, N. K. Synthesis of N-isoindolinonyl peptides via Pd-catalyzed C(sp2)-H olefination-activation and their conformational studies. Organic & biomolecular chemistry 2023, 21, 5104–5116. doi:10.1039/d3ob00742a
• Li, Y.; Li, Y.; Fei, H.; Kong, R.; Yu, Z.; He, L. Synthesis of 3-(2-oxopropyl)-2-arylisoindolinone derivatives via a three-component reaction of diaryliodonium salts with 2-formylbenzonitriles and phenylacetylenes. Journal of Chemical Research 2022, 46. doi:10.1177/17475198211063799
• Zhao, H.; Yang, D.; Xu, H.; Huang, D. Rhodium(III)-Catalyzed Intramolecular Benzylic C(sp3)–H Amidation for the Synthesis of Isoindolinones. Synthesis 2022, 55, 481–488. doi:10.1055/a-1954-4920
• Liu, H.; You, X.; Wen, F.; Zhang, Z.; Li, Z. Calcium Carbide as a Surrogate of Acetylene: Copper‐Catalyzed Construction of 3‐Methylene‐2‐arylisoindolin‐1‐ones. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200204
• Du, X.; Hu, Y.; Yang, D.; Huang, D.; Yang, W.; Wu, H.; Zhao, H. Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C-H/N-H annulation of N-methoxy benzamides with saturated ketones. Organic & biomolecular chemistry 2022, 20, 783–789. doi:10.1039/d1ob02166d
• Gupta, M. K.; Jena, C. K.; Sharma, N. K. Pd-Catalyzed C(sp2)-H olefination: synthesis of N-alkylated isoindolinone scaffolds from aryl amides of amino acid esters. Organic & biomolecular chemistry 2021, 19, 10097–10104. doi:10.1039/d1ob01997j
• Buglioni, L.; Raymenants, F.; Slattery, A.; Zondag, S. D. A.; Noël, T. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry. Chemical reviews 2021, 122, 2752–2906. doi:10.1021/acs.chemrev.1c00332
• Rehm, T. H.
• Rehm, T. H. Photochemistry in Flow for Drug Discovery. Topics in Medicinal Chemistry; Springer International Publishing, 2021; pp 71–119. doi:10.1007/7355_2021_112
• Savela, R.; Méndez-Gálvez, C. Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 5344–5378. doi:10.1002/chem.202004375
• Yaseen, M. A.; Mumtaz, S.; Hunter, R.; Wall, D.; Robertson, M. J.; Oelgemöller, M. Continuous-flow photochemical transformations of 1,4-naphthoquinones and phthalimides in a concentrating solar trough reactor. Australian Journal of Chemistry 2020, 73, 1149–1157. doi:10.1071/ch20138
• Mumtaz, S.; Robertson, M. J.; Oelgemöller, M. Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones. Molecules (Basel, Switzerland) 2019, 24, 4527. doi:10.3390/molecules24244527
• Mumtaz, S.; Robertson, M. J.; Oelgemöller, M. Recent Advances in Photodecarboxylations Involving Phthalimides. Australian Journal of Chemistry 2018, 71, 634–648. doi:10.1071/ch18220

Explore citations to this article at