TY - JOUR
T1 - Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir
AU - Miele, Margherita
AU - Castoldi, Laura
AU - Prado-Roller, Alexander
AU - Pisano, Luisa
AU - Pace, Vittorio
N1 - Publisher Copyright:
© 2024 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
PY - 2024/10/14
Y1 - 2024/10/14
N2 - 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.
AB - 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.
KW - Isocyanates Amides Chemoselecivity Nitriles Nucleophilic addition
UR - http://www.scopus.com/inward/record.url?scp=85205357961&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202400619
DO - 10.1002/ejoc.202400619
M3 - Article
AN - SCOPUS:85205357961
SN - 1434-193X
VL - 27
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 39
M1 - e202400619
ER -