TY - JOUR
T1 - Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals
AU - Cannalire, Rolando
AU - Amato, Jussara
AU - Summa, Vincenzo
AU - Novellino, Ettore
AU - Tron, Gian Cesare
AU - Giustiniano, Mariateresa
N1 - Publisher Copyright:
© 2020 American Chemical Society. All rights reserved.
PY - 2020/11/6
Y1 - 2020/11/6
N2 - A new visible light-induced photocatalytic protocol enabling the formation of secondary amides from electron-poor organic bromides and isocyanides was developed. In addition, the in situ interception of ketenimine intermediates with nitrogen nucleophiles such as amines, hydrazines, and TMSN3 afforded, in a one-pot two-step procedure, valuable scaffolds such as ketene aminals, pyrazolones, and tetrazoles. Mechanistic evidence confirmed a radical pathway where isocyanides acted as radical geminal acceptors generating key imidoyl radical species.
AB - A new visible light-induced photocatalytic protocol enabling the formation of secondary amides from electron-poor organic bromides and isocyanides was developed. In addition, the in situ interception of ketenimine intermediates with nitrogen nucleophiles such as amines, hydrazines, and TMSN3 afforded, in a one-pot two-step procedure, valuable scaffolds such as ketene aminals, pyrazolones, and tetrazoles. Mechanistic evidence confirmed a radical pathway where isocyanides acted as radical geminal acceptors generating key imidoyl radical species.
UR - http://www.scopus.com/inward/record.url?scp=85096198064&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c01946
DO - 10.1021/acs.joc.0c01946
M3 - Article
SN - 0022-3263
VL - 85
SP - 14077
EP - 14086
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -