The direct addition of a nitrile anion to isocyanates is reported for a straightforward preparation of valuable cyanoformamides. Through the proper activation of an adequate silicon-ate complex precursor (PhMe2SiCN) with a Lewis base (potassium tert-amylate) under Barbier-type conditions, the cyanide was instantaneously released, thus yielding the desired motif with full chemocontrol. No particular structural restriction was noticed for engaging in the transformation a wide series of commercially available isocyanates.
Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir / M. Miele, L. Castoldi, E.M. Beccalli, V. Pace. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 27:39(2024 Oct 14), pp. e202400619.1-e202400619.5. [Epub ahead of print] [10.1002/ejoc.202400619]
Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir
L. CastoldiSecondo
;E.M. BeccalliPenultimo
;
2024
Abstract
The direct addition of a nitrile anion to isocyanates is reported for a straightforward preparation of valuable cyanoformamides. Through the proper activation of an adequate silicon-ate complex precursor (PhMe2SiCN) with a Lewis base (potassium tert-amylate) under Barbier-type conditions, the cyanide was instantaneously released, thus yielding the desired motif with full chemocontrol. No particular structural restriction was noticed for engaging in the transformation a wide series of commercially available isocyanates.File | Dimensione | Formato | |
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Eur J Org Chem - 2024 - Miele - Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile.pdf
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