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Angewandte Chemie International Edition

Angewandte Chemie International Edition

IF: 16.1
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A Boron Scan of Ethyl Acetoacetate Leads to Versatile Building Blocks

Published:26 January 2024 DOI: 10.1002/anie.202319842
Alina Trofimova, Brandon White, Diego B. Diaz, Martynas J. ?irvinskas, Alan Lough, Travis Dudding, Andrei K. Yudin

Abstract

Discovered in the 19th century, ethyl acetoacetate has been central to the development of organic chemistry, including its pedagogy and applications. In this study, we present borylated derivatives of this venerable molecule. A boron handle has been installed at either - or -position of acetoacetate by homologation of acyl-MIDA (N-methyliminodiacetic acid) boronates with diazoacetates. Either alkyl or boryl groups were found to migrate with regiochemistry being a function of the steric bulk of the diazo species. Boryl -ketoesters can be further modified into borylated pyrazolones and oximes, thereby expanding the synthetic toolkit and offering opportunities for additional modifications.

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Procduct Name CAS Molecular Formula Supplier Price
Ethyl acetoacetate 141-97-9 C6H10O3 892 suppliers $5.00-$4272.16
3,5-Dimethylpyrazole 67-51-6 C5H8N2 634 suppliers $6.00-$1720.00
N-Methyliminodiacetic acid 4408-64-4 C5H9NO4 231 suppliers $6.00-$380.80
N-METHYL CARBAMOYL OXIMES & N-METHYL CARBAMATES 1 suppliers Inquiry

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