TY - JOUR
T1 - Cascade Synthesis of Benzimidazole-Linked Pyrroles via Copper Catalyzed Oxidative Cyclization and Ketonization
AU - Ye, Tzuen Yang
AU - Selvaraju, Manikandan
AU - Sun, Chung-Ming
PY - 2017/6/16
Y1 - 2017/6/16
N2 - A three-component cascade reaction of 2-aminobenzimidazole, aldehyde, and terminal alkyne has been explored for an efficient synthesis of benzimidazole-linked tetrasubstituted pyrroles. The reaction sequence involves the formation of propargylamine, insertion of a terminal alkyne, and a ring opening reaction followed by an intramolecular carbonylative cyclization under aerobic conditions. It represents a novel strategy to the construction of C=N, C=C, C=O bonds and a new five-membered 2-ketopyrrole ring. In this process, the reaction conditions are crucial and an attempt to elucidate the novel reaction pathway is well supported by X-ray crystallography.
AB - A three-component cascade reaction of 2-aminobenzimidazole, aldehyde, and terminal alkyne has been explored for an efficient synthesis of benzimidazole-linked tetrasubstituted pyrroles. The reaction sequence involves the formation of propargylamine, insertion of a terminal alkyne, and a ring opening reaction followed by an intramolecular carbonylative cyclization under aerobic conditions. It represents a novel strategy to the construction of C=N, C=C, C=O bonds and a new five-membered 2-ketopyrrole ring. In this process, the reaction conditions are crucial and an attempt to elucidate the novel reaction pathway is well supported by X-ray crystallography.
UR - http://www.scopus.com/inward/record.url?scp=85020939310&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.7b01224
DO - 10.1021/acs.orglett.7b01224
M3 - Article
C2 - 28580783
AN - SCOPUS:85020939310
SN - 1523-7060
VL - 19
SP - 3103
EP - 3106
JO - Organic Letters
JF - Organic Letters
IS - 12
ER -