REFERENCES

1. Crespi, S.; Fagnoni, M. Generation of alkyl radicals: from the tyranny of tin to the photon democracy. Chem. Rev. 2020, 120, 9790-833.

2. Xuan, J.; Zhang, Z. G.; Xiao, W. J. Visible-light-induced decarboxylative functionalization of carboxylic acids and their derivatives. Angew. Chem. Int. Ed. Engl. 2015, 54, 15632-41.

3. Jin, Y.; Fu, H. Visible-light photoredox decarboxylative couplings. Asian. J. Org. Chem. 2017, 6, 368-85.

4. Kitcatt, D. M.; Nicolle, S.; Lee, A. L. Direct decarboxylative Giese reactions. Chem. Soc. Rev. 2022, 51, 1415-53.

5. Schwarz, J.; König, B. Decarboxylative reactions with and without light - a comparison. Green. Chem. 2018, 20, 323-61.

6. Nicewicz, D. A.; MacMillan, D. W. Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 2008, 322, 77-80.

7. Zheng, S.; Primer, D. N.; Molander, G. A. Nickel/photoredox-catalyzed amidation via alkylsilicates and isocyanates. ACS. Catal. 2017, 7, 7957-61.

8. Molander, G. A. Organotrifluoroborates: another branch of the mighty oak. J. Org. Chem. 2015, 80, 7837-48.

9. Campbell, M. W.; Compton, J. S.; Kelly, C. B.; Molander, G. A. Three-component olefin dicarbofunctionalization enabled by nickel/photoredox dual catalysis. J. Am. Chem. Soc. 2019, 141, 20069-78.

10. Schwarz, J. L.; Kleinmans, R.; Paulisch, T. O.; Glorius, F. 1,2-Amino alcohols via Cr/photoredox dual-catalyzed addition of α-amino carbanion equivalents to carbonyls. J. Am. Chem. Soc. 2020, 142, 2168-74.

11. Yu, X. Y.; Chen, J. R.; Wang, P. Z.; Yang, M. N.; Liang, D.; Xiao, W. J. A visible-light-driven iminyl radical-mediated C-C single bond cleavage/radical addition cascade of oxime esters. Angew. Chem. Int. Ed. Engl. 2018, 57, 738-43.

12. Klauck, F. J. R.; James, M. J.; Glorius, F. Deaminative strategy for the visible-light-mediated generation of alkyl radicals. Angew. Chem. Int. Ed. Engl. 2017, 56, 12336-9.

13. Wu, J.; Grant, P. S.; Li, X.; Noble, A.; Aggarwal, V. K. Catalyst-free deaminative functionalizations of primary amines by photoinduced single-electron transfer. Angew. Chem. Int. Ed. Engl. 2019, 58, 5697-701.

14. Baumann, M.; Baxendale, I. R. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles. Beilstein. J. Org. Chem. 2013, 9, 2265-319.

15. Vitaku, E.; Smith, D. T.; Njardarson, J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 2014, 57, 10257-74.

16. Yuan, X. Y.; Si, Y. F.; Li, X.; et al. Decatungstate-photocatalyzed direct coupling of inert alkanes and quinoxalin-2(1H)-ones with H2 evolution. Org. Chem. Front. 2022, 9, 2728-33.

17. Cheng, F.; Fan, L.; Lv, Q.; Chen, X.; Yu, B. Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics. Green. Chem. 2023, 25, 7971-7.

18. Xu, J.; Cai, H.; Shen, J.; et al. Photo-induced cross-dehydrogenative alkylation of heteroarenes with alkanes under aerobic conditions. J. Org. Chem. 2021, 86, 17816-32.

19. Liang, X. A.; Niu, L.; Wang, S.; Liu, J.; Lei, A. Visible-light-induced C(sp3)-H oxidative arylation with heteroarenes. Org. Lett. 2019, 21, 2441-4.

20. Zhang, L.; He, J.; Zhang, P.; Zheng, K.; Shen, C. Visible-light-induced decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates by cerium photocatalysis. Mol. Catal. 2022, 519, 112145.

21. Niu, K.; Jiao, H.; Zhou, P.; Wang, Q. Photoinduced direct electron transfer between quinoxalin-2(1H)-ones and alkyl carboxylic acids for C-H alkylation. Org. Lett. 2023, 25, 8970-4.

22. Wang, M.; Liu, J.; Zhang, Y.; Sun, P. Decarbonylative C3-alkylation of quinoxalin-2(1H)-ones with aliphatic aldehydes via photocatalysis. Adv. Synth. Catal. 2022, 364, 2660-5.

23. Zhang, H.; Xu, J.; Ouyang, Y.; et al. Molecular oxygen-mediated selective hydroxyalkylation and alkylation of quinoxalin-2(1H)-ones with alkylboronic acids. Chinese. Chem. Lett. 2022, 33, 2036-40.

24. Xu, J.; Liang, C.; Shen, J.; Chen, Q.; Li, W.; Zhang, P. Photoinduced, metal- and photosensitizer-free decarboxylative C–H (amino)alkylation of heteroarenes in a sustainable solvent. Green. Chem. 2023, 25, 1975-81.

25. Xie, L.; Peng, S.; Fan, T.; et al. Metal-free C3-alkoxycarbonylation of quinoxalin-2(1H)-ones with carbazates as ecofriendly ester sources. Sci. China. Chem. 2019, 62, 460-4.

26. Sun, J.; Yang, H.; Zhang, B. Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins with unactivated alkyl iodides. Green. Chem. 2022, 24, 858-63.

27. He, X. K.; Lu, J.; Zhang, A. J.; Zhang, Q. Q.; Xu, G. Y.; Xuan, J. BI-OAc-accelerated C3-H alkylation of quinoxalin-2(1H)-ones under visible-light irradiation. Org. Lett. 2020, 22, 5984-9.

28. Guo, Y.; Luo, J.; Tan, S.; Otieno, B. O.; Zhang, Z. The applications of vitamin E TPGS in drug delivery. Eur. J. Pharm. Sci. 2013, 49, 175-86.

29. Williams, S. J. Sulfatase inhibitors: a patent review. Expert. Opin. Ther. Pat. 2013, 23, 79-98.

30. Wang, J.; Liu, X.; Wu, Z.; et al. Silver-catalyzed decarboxylative C–H functionalization of cyclic aldimines with aliphatic carboxylic acids. Chinese. Chem. Lett. 2021, 32, 2777-81.

31. Wang, J.; Liu, X.; Wu, Z.; et al. Ag-catalyzed ring-opening of tertiary cycloalkanols for C-H functionalization of cyclic aldimines. Chem. Commun. 2021, 57, 1506-9.

32. Fang, L.; Yu, J.; Yu, Z.; et al. Photoinduced metal- and photosensitizer-free decarbonylative C-H alkylation of cyclic sulfamidate imines. J. Org. Chem. 2023, 88, 17249-56.

33. Zhang, J.; Li, X.; Liao, L.; Liu, H.; Luo, H. Catalyst-free, air-mediated C(sp2)−H alkylation of cyclic aldimines with alkylboronic acids. Adv. Synth. Catal. 2023, 365, 4544-9.

34. Song, H.; Xiao, F.; Jiang, J.; et al. External photocatalyst-free C-H alkylation of N-sulfonyl ketimines with alkanes under visible light. Chinese. Chem. Lett. 2023, 34, 108509.

35. Yi, H.; Zhang, G.; Wang, H.; et al. Recent advances in radical C-H activation/radical cross-coupling. Chem. Rev. 2017, 117, 9016-85.

36. Chirik, P.; Morris, R. Getting down to earth: the renaissance of catalysis with abundant metals. Acc. Chem. Res. 2015, 48, 2495.

37. Yuan, X.; Wang, C.; Yu, B. Recent advances in FeCl3-photocatalyzed organic reactions via hydrogen-atom transfer. Chinese. Chem. Lett. 2024, 35, 109517.

38. de Groot, L. H. M.; Ilic, A.; Schwarz, J.; Wärnmark, K. Iron photoredox catalysis-past, present, and future. J. Am. Chem. Soc. 2023, 145, 9369-88.

39. Stahl, J.; König, B. A survey of the iron ligand-to-metal charge transfer chemistry in water. Green. Chem. 2024, 26, 3058-71.

40. Fernández-García, S.; Chantzakou, V. O.; Juliá-Hernández, F. Direct decarboxylation of trifluoroacetates enabled by iron photocatalysis. Angew. Chem. Int. Ed. Engl. 2024, 63, e202311984.

41. Li, Z.; Wang, X.; Xia, S.; Jin, J. Ligand-accelerated iron photocatalysis enabling decarboxylative alkylation of heteroarenes. Org. Lett. 2019, 21, 4259-65.

42. Jin, Y.; Zhang, Q.; Wang, L.; Wang, X.; Meng, C.; Duan, C. Convenient C(sp3)–H bond functionalisation of light alkanes and other compounds by iron photocatalysis. Green. Chem. 2021, 23, 6984-9.

43. Xia, G. D.; Liu, Z. K.; Zhao, Y. L.; Jia, F. C.; Hu, X. Q. Radical phosphorylation of aliphatic C-H bonds via iron photocatalysis. Org. Lett. 2023, 25, 5279-84.

44. Kang, Y. C.; Treacy, S. M.; Rovis, T. Iron-catalyzed photoinduced LMCT: a 1° C-H abstraction enables skeletal rearrangements and C(sp3)-H alkylation. ACS. Catal. 2021, 11, 7442-9.

45. Tu, J. L.; Hu, A. M.; Guo, L.; Xia, W. Iron-catalyzed C(Sp3)-H borylation, thiolation, and sulfinylation enabled by photoinduced ligand-to-metal charge transfer. J. Am. Chem. Soc. 2023, 145, 7600-11.

46. Zhang, Z.; Li, X.; Zhou, D.; Ding, S.; Wang, M.; Zeng, R. Controllable C-H alkylation of polyethers via iron photocatalysis. J. Am. Chem. Soc. 2023, 145, 7612-20.

47. Niu, K.; Shi, X.; Ding, L.; Liu, Y.; Song, H.; Wang, Q. HCl-catalyzed aerobic oxidation of alkylarenes to carbonyls. ChemSusChem 2022, 15, e202102326.

48. Lu, Y.; Mu, S.; Li, H.; et al. EtOH-catalyzed electrosynthesis of imidazolidine-fused sulfamidates from N-sulfonyl ketimines, N-arylglycines and formaldehyde. Green. Chem. 2023, 25, 5539-42.

Chemical Synthesis
ISSN 2769-5247 (Online)

Portico

All published articles are preserved here permanently:

https://www.portico.org/publishers/oae/

Portico

All published articles are preserved here permanently:

https://www.portico.org/publishers/oae/