Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion <i>Reservoir</i>
- Author(s)
- Margherita Miele, Laura Castoldi, Alexander Prado-Roller, Luisa Pisano, Vittorio Pace
- 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.
- Organisation(s)
- Department of Pharmaceutical Sciences, Core Facility Crystal Structure Analysis, Department of Inorganic Chemistry
- External organisation(s)
- Università degli Studi di Torino, Università degli Studi di Milano-Bicocca, Università degli Studi di Sassari
- Journal
- European Journal of Organic Chemistry
- Volume
- 27
- ISSN
- 1434-193X
- DOI
- https://doi.org/10.1002/ejoc.202400619
- Publication date
- 2024
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 301207 Pharmaceutical chemistry, 104015 Organic chemistry
- Keywords
- ASJC Scopus subject areas
- Physical and Theoretical Chemistry, Organic Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/2e57897e-5fcd-4388-b027-a7195628aecf