A versatile synthesis of substituted benzimidazolium salts by an amination/ring closure sequence.
[reaction: see text]. A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha-chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.
Rivas
F M
FM
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA.
Riaz
U
U
Giessert
A
A
Smulik
J A
JA
Diver
S T
ST
D000588:Amines / Q000737:chemistry*; D001562:Benzimidazoles / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts; D013816:Thermodynamics
D000588:Amines; D001562:Benzimidazoles; D005663:Furans; D011714:Pyrans; D012492:Salts; C018674:tetrahydrofuran