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Synthesis 2025; 57(05): 965-972
DOI: 10.1055/a-2412-9549
DOI: 10.1055/a-2412-9549
feature
The Acylation of α-Carbonyl Sulfoxonium Ylides with N-Hydroxyphthalimide Esters
The authors would like to thank the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (São Paulo State Research Foundation) (2023/02675-7) and the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (National Council for Scientific and Technological Development) (307237/2021-4) for financial support. E.F.M. is grateful to Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (Coordination for the Improvement of Higher Education Personnel) for a fellowship. We are also grateful for support from FAPESP via the Research Centre for Greenhouse Gas Innovation (RCGI), hosted by the University of São Paulo (USP) and sponsored by the FAPESP–São Paulo Research Foundation (2020/15230-5), Shell Brasil, and for the strategic importance of the support given by Agência Nacional do Petróleo, Gás Natural e Biocombustíveis (ANP) (Brazil’s National Oil, Natural Gas and Biofuels Agency) through the R&D levy regulation.
Abstract
A new method for the synthesis of 1,3-dicarbonyl sulfoxonium ylides is described. This acylation reaction is carried out under mild conditions using inexpensive and bench-stable N-hydroxyphthalimide esters as acylating agents. The reactions proceed via a non-radical, transition-metal-free pathway, and the corresponding products are obtained in yields of up to 85%.
Key words
sulfur ylides - sulfoxonium ylides - acylation - N-hydroxyphthalimide - dicarbonyl compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2412-9549.
- Supporting Information
Publication History
Received: 02 August 2024
Accepted after revision: 10 September 2024
Accepted Manuscript online:
10 September 2024
Article published online:
02 October 2024
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References
- 1 Bisag GD, Ruggieri S, Fochi M, Bernardi L. Org. Biomol. Chem. 2020; 18: 8793
- 2 Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1962; 84: 867
- 3 Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1965; 87: 1353
- 4 Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1964; 86: 1640
- 5 Johnson AW, LaCount RB. J. Am. Chem. Soc. 1961; 83: 417
- 6 Caiuby CA. D, Furniel LG, Burtoloso AC. B. Chem. Sci. 2022; 13: 1192
- 7 Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
- 8 Baldwin JE, Adlington RM, Godfrey CR. A, Gollins DW, Vaughan JG. J. Chem. Soc., Chem. Commun. 1993; 1434
- 9 Caiuby CA. D, de Jesus MP, Burtoloso AC. B. J. Org. Chem. 2020; 85: 7433
- 10 Kumar A, Sherikar MS, Hanchate V, Prabhu KR. Tetrahedron 2021; 101: 132478
- 11 Wu X, Sun S, Yu J.-T, Cheng J. Synlett 2019; 30: 21
- 12 Gallo RD. C, Ahmad A, Metzker G, Burtoloso AC. B. Chem. Eur. J. 2017; 23: 16980
- 13 Day DP, Mora Vargas JA, Burtoloso AC. B. J. Org. Chem. 2021; 86: 12427
- 14 Sarabia F, Martín-Gálvez F, Chammaa S, Martín-Ortiz L, Sánchez-Ruiz A. J. Org. Chem. 2010; 75: 5526
- 15 de Souza JH, Vargas JA. M, Burtoloso AC. B. Synthesis 2024; 56: 758
- 16 Janot C, Chagnoleau J.-B, Halcovitch NR, Muir J, Aïssa C. J. Org. Chem. 2020; 85: 1126
- 17 Yuan Y, Wu X.-F. Org. Lett. 2019; 21: 5310
- 18 Vaitla J, Hopmann KH, Bayer A. Org. Lett. 2017; 19: 6688
- 19 Dost F, Gosselck J. Tetrahedron Lett. 1970; 11; 5091
- 20 Echemendía R, To AJ, Murphy GK, Burtoloso AC. B. Adv. Synth. Catal. 2024; 366: 396
- 21 Talero AG, Martins BS, Burtoloso AC. B. Org. Lett. 2018; 20: 7206
- 22 Barday M, Janot C, Halcovitch NR, Muir J, Aïssa C. Angew. Chem. Int. Ed. 2017; 56: 13117
- 23 de Jesus MP, Echemendía R, Burtoloso AC. B. Org. Chem. Front. 2023; 10: 3577
- 24 Li Y, Ge L, Muhammad M, Bao H. Synthesis 2017; 49: 5263
- 25 Laudadio G, Palkowitz MD, El-Hayek Ewing T, Baran PS. ACS Med. Chem. Lett. 2022; 13: 1413
- 26 Cornella J, Edwards JT, Qin T, Kawamura S, Wang J, Pan C.-M, Gianatassio R, Schmidt M, Eastgate MD, Baran PS. J. Am. Chem. Soc. 2016; 138: 2174
- 27 Toriyama F, Cornella J, Wimmer L, Chen T.-G, Dixon DD, Creech G, Baran PS. J. Am. Chem. Soc. 2016; 138: 11132
- 28 Xuan J, Zhang Z, Xiao W. Angew. Chem. Int. Ed. 2015; 54: 15632
- 29 Correia JT. M, Piva da Silva G, Kisukuri CM, André E, Pires B, Carneiro PS, Paixão MW. J. Org. Chem. 2020; 85: 9820
- 30 Echemendía R, de Oliveira KT, Burtoloso AC. B. Org. Lett. 2022; 24: 6386
- 31 Allen LJ, Cabrera PJ, Lee M, Sanford MS. J. Am. Chem. Soc. 2014; 136: 5607
- 32 Yang Z, Tang J, Chen Z, Wu X.-F. Org. Lett. 2022; 24: 7288
- 33 Yang T, Jiang Y, Luo Y, Lim JJ. H, Lan Y, Koh MJ. J. Am. Chem. Soc. 2020; 142: 21410