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. Castoldi
Secondo
;
E.M. Beccalli
Penultimo
;
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.
Isocyanates Amides Chemoselecivity Nitriles Nucleophilic addition;
Settore CHEM-05/A - Chimica organica
14-ott-2024
10-lug-2024
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1122233
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