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Updated: Apr 15, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
Published on: March 25, 2017
Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles
Sabin Llona-Minguez1, Matthieu Desroses, Artin Ghassemian
1Science for Life Laboratory, Division of Translational, Medicine & Chemical Biology, Department of Medical Biochemistry & Biophysics, Karolinska Institutet, Stockholm, 171 21 (Sweden) http://www.helleday.org. sabin.llona.minguez@scilifelab.se.
Abstract:
A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.
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