Formyl MIDA Boronate: C 1 Building Block Enables Straightforward Access to α-Functionalized Organoboron Derivatives

• Published in: Angewandte Chemie International Edition Vol. 59; no. 41; pp. 18016 - 18022
• Main Authors: Ivon, Yevhen M, Mazurenko, Ivan V, Kuchkovska, Yuliya O, Voitenko, Zoya V, Grygorenko, Oleksandr O
• Format: Journal Article
• Language: English
• Published: Germany 05-10-2020
• Subjects: oxidation; aldehydes; boron; C1 building blocks; synthetic methods
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202007651

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 C
building block for extending the scope of organoboron chemistry.