Literature DB >> 32621386

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

Yevhen M Ivon1,2, Ivan V Mazurenko1,2, Yuliya O Kuchkovska1,2, Zoya V Voitenko2, Oleksandr O Grygorenko1,2.   

Abstract

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.
© 2020 Wiley-VCH GmbH.

Entities:  

Keywords:  C1 building blocks; aldehydes; boron; oxidation; synthetic methods

Year:  2020        PMID: 32621386     DOI: 10.1002/anie.202007651

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

Authors:  Lucia Wang; Shengjia Lin; Yawei Zhu; Daniel Ferrante; Timaf Ishak; Yuki Baba; Abhishek Sharma
Journal:  Chem Commun (Camb)       Date:  2021-04-12       Impact factor: 6.222

2.  A Convenient, Rapid, Conventional Heating Route to MIDA Boronates.

Authors:  Andrew McGown; Anthony K Edmonds; Daniel Guest; Verity L Holmes; Chris Dadswell; Ramón González-Méndez; Charles A I Goodall; Mark C Bagley; Barnaby W Greenland; John Spencer
Journal:  Molecules       Date:  2022-08-09       Impact factor: 4.927

3.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

Authors:  Shengjia Lin; Lucia Wang; Abhishek Sharma
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

4.  Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3 -Synthons.

Authors:  Max Wienhold; John J Molloy; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-09       Impact factor: 16.823

  4 in total

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