Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling. Issue 25 (17th June 2015)

• Record Type: Journal Article
• Authors: Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro
• Is Part Of: Tetrahedron letters. Volume 56:Issue 25(2015)
• Page Start: 3855
• Page End: 3857
• Publication Date: 2015-06-17
• Subjects: Imidazoles -- Sonogashira reaction -- Regioselectivity -- Aromatic bromination -- Alkynylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.094
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A variety of 2-substituted 5-alkynyl-1 H -imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1, 2-dimethyl-1 H -imidazole, 2-chloro-1-methyl-1 H -imidazole, and 2-aryl-1-methyl-1 H- imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation.