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Synthesis
DOI: 10.1055/a-2412-9549
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The Acylation of α-Carbonyl Sulfoxonium Ylides with N-Hydroxyphthalimide Esters

Eduardo F. Mizobuchi
,
Antonio C. B. Burtoloso  ∗
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.
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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 compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2412-9549.
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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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