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Synthesis
DOI: 10.1055/a-2314-1877
paper

Modular Synthesis of Conjugated Aromatic Boronate Esters by Radical Xanthate Addition

Congze He
a   State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, P. R. of China
b   Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, Route de Scalay, 91128 Palaiseau Cedex, France
,
Xiangcheng Pan∗
a   State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, P. R. of China
,
Samir Z. Zard∗
b   Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, Route de Scalay, 91128 Palaiseau Cedex, France
› InstitutsangabenWe thank the China Scholarship Council (scholarship to C.H.), the National Natural Science Foundation of China (22322103 and 22271057), the Natural Science Foundation of Shanghai Municipality (22ZR1406000), and the State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University for support.
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Abstract

Conjugated aromatic boronate esters serve as crucial intermediates in the synthesis of pharmaceuticals and polymer materials. Traditional methods for their synthesis typically involve organoboration of aromatic ring compounds, where pre-constructions of aromatic rings are required. Here, we present a general strategy for the synthesis of diverse conjugated aromatic boronate esters based on the radical addition of xanthates. Through this method, we synthesized various boronate ester xanthates that could be utilized as a platform to furnish conjugated aromatic building blocks, including thiophenes, pyrroles, tetralones, naphthols, and naphthylamines. This cost-effective strategy holds promise as a viable method for the industrial-scale production of (hetero)aromatic boronate esters.

Key words

xanthates - radical addition - boronates - aromatic compounds - modular synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2314-1877.
  • Supporting Information


Publikationsverlauf

Eingereicht: 21. März 2024

Angenommen nach Revision: 25. April 2024

Accepted Manuscript online:
25. April 2024

Artikel online veröffentlicht:
21. Mai 2024

© 2024. Thieme. All rights reserved

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