A versatile synthesis of substituted benzimidazolium salts by an amination/ring closure sequence

Citation
Fm. Rivas et al., A versatile synthesis of substituted benzimidazolium salts by an amination/ring closure sequence, ORG LETT, 3(17), 2001, pp. 2673-2676
Citations number
53
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
17
Year of publication
2001
Pages
2673 - 2676
Database
ISI
SICI code
1523-7060(20010823)3:17<2673:AVSOSB>2.0.ZU;2-J
Abstract
[GRAPHICS] A new method to produce benzimidazolium salts based on a successive Buchwal d-Hartwig amination and ring closure is reported. A variety of different be nzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazoli um salts. The salts that lack a C2 substituent on the heterocycle are readi ly deprotonated to give nucleophilic carbenes.