Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2024; 35(03): 297-302
DOI: 10.1055/a-2131-4033
DOI: 10.1055/a-2131-4033
cluster
Organic Chemistry Under Visible Light: Photolytic and Photocatalytic Organic Transformations
A Computational and Experimental Analysis of Aldehyde Photooxidation Driven by Visible Light in a Homemade Reactor
J.C.G. and S.E.M.R. are grateful to the Consejo Nacional de Ciencia y Tecnología (CONACyT)-Mexico (grants 395719 and 1000464, respectively) and Catedra-CONACyT Project 781 (LACAPFEM-UGUAA-CONACYT, 316011).
Abstract
A computational and experimental analysis of HAT mechanism to obtain carboxylic acid via photooxidation of aldehyde is described, using a homemade reactor. The considered photocatalysts are organic dyes such as 2-chloroanthraquinone (2-ClAQN), rhodamine 6G (Rh6G), fluorescein (Fl), and eosin B (EOB); and the light spectrum is that of the visible light.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2131-4033.
- Supporting Information
Publication History
Received: 30 May 2023
Accepted after revision: 17 July 2023
Accepted Manuscript online:
17 July 2023
Article published online:
04 September 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 2 Albini A, Fagnoni M. Green Chem. 2004; 6: 1
- 3 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 4 Schöneich C. Hydrogen Atom Transfer in Model Reactions. In Hydrogen-Transfer Reactions. John Wiley & Sons; Hoboken: 2006
- 5 Capaldo L, Quadri LL, Ravelli D. Green Chem. 2020; 22: 3376
- 6 Milan M, Salamone M, Costas M, Biette M. Acc. Chem. Res. 2018; 51: 1984
- 7 Caoaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2056
- 8 Garavelli M. Theor. Chem. Acc. 2006; 116: 87
- 9 Liu Y, Roca-Sanjuán D, Lindh R. In Photochemistry. Albini A, Fasani E. The Royal Society of Chemistry; 2012. 40, 42
- 10 Green Oxidative Synthesis of Carboxylic Acids. Liu M, Li C.-J. John Wiley and Sons; Hoboken: 2019
- 11 Tian Q, Shi D, Sha Y. Molecules 2008; 13: 948
- 12 König B. Eur. J. Org. Chem. 2017; 1979
- 13 Michelin C, Hoffmann N. ACS Catal. 2018; 8: 12046
- 14 Fagnoni M, Dondi D, Ravelli D. Chem. Rev. 2007; 107: 2725
- 15 Itoh A, Hashimoto S, Masaki Y. Synlett 2005; 2639
- 16 Hirashima SI, Itoh A. Chem. Pharm. Bull. 2007; 55: 156
- 17 Iqbal N, Choi S, You Y, Cho EJ. Tetrahedron Lett. 2013; 54: 6222
- 18 Amos SG. E, Garreau M, Buzzetti L, Waser J. Beilstein J. Org. Chem. 2020; 16: 1163
- 19 Tada N, Hattori K, Nobuta T, Miura T, Itoh A. Green Chem. 2011; 13: 1669
- 20 Cervantes-González J, Vosburg DA, Mora-Rodriguez SE, Vázquez MA, Zepeda LG, Villegas Gómez C, Lagunas-Rivera S. ChemCatChem 2020; 12: 3811
- 21 Zhang W, Gacs J, Arends IW. C. E, Hollmann F. ChemCatChem 2017; 9: 3821
- 22 A solution of benzaldehyde (1, 1 equiv), 2-ClAQN as photocatalyst (0.1 equiv), and K2CO3 (0.05 equiv) in EtOAc (1 mL), and the mixture was stirred and irradiated under visible-light radiation with 23 W fluorescent bulbs and O2 (atm) during 4 h. After the reaction time, 1.0 mL of 10% NaHCO3 solution was added to the reaction, and the organic phase was separated from the aqueous phase. Subsequently, the aqueous phase was added to a 2.0 N HCl solution, and it was extracted with EtOAc (3 × 10 mL), anhydrous Na2SO4 was added to the organic phase, filtered, and evaporated under reduced pressure to obtain the product 2.