Formyl MIDA Boronate: C1 Building Block Enables Straightforward Access to α‐Functionalized Organoboron Derivatives

Formyl MIDA boronate has been known to be an elusive type of acylboronate that has not been obtained to date. In this work, an approach to the one‐pot preparation and chemical transformations of formyl MIDA boronate were developed to provide new types of α‐functionalized organoboron compounds. Among...

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Veröffentlicht in:Angewandte Chemie International Edition 2020-10, Vol.59 (41), p.18016-18022
Hauptverfasser: Ivon, Yevhen M., Mazurenko, Ivan V., Kuchkovska, Yuliya O., Voitenko, Zoya V., Grygorenko, Oleksandr O.
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Sprache:eng
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Zusammenfassung:Formyl MIDA boronate has been known to be an elusive type of acylboronate that has not been obtained to date. In this work, an approach to the one‐pot preparation and chemical transformations of formyl MIDA boronate were developed to provide new types of α‐functionalized organoboron compounds. Among them are acylboronate reagents which present boron‐substituted analogues of ynones and β‐dicarbonyl compounds. The developed synthetic procedures, utilizing formyl MIDA boronate, are tolerant to diverse functional groups, making this reagent an advantageous C1 building block for extending the scope of organoboron chemistry. One‐pot preparation and chemical reactions of formyl MIDA boronate are described in this work. New types of α‐functionalized organoboron compounds, including boron‐substituted analogues of ynones and β‐dicarbonyl compounds, are synthesized. The method demonstrates high tolerance to diverse functional moieties, making formyl MIDA boronate a valuable C1 building block for extending the scope of organoboron chemistry.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202007651