An efficient synthesis of carboranyl tetrazoles via alkylation of 5-R-1H-tetrazoles with allylcarboranes. (5th September 2016)

• Record Type: Journal Article
• Authors: Ol'shevskaya, Valentina A.; Makarenkov, Anton V.; Kononova, Elena G.; Peregudov, Alexander S.; Lyssenko, Konstantin A.; Kalinin, Valery N.
• Is Part Of: Polyhedron. Volume 115(2016)
• Page Start: 128
• Page End: 136
• Publication Date: 2016-09-05
• Subjects: Carboranes -- Heterocycles -- Tetrazoles -- Acid catalysis -- Alkylation; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2016.05.006
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: The regioselective synthesis of new o - and m -carborane tetrazoles was developed via the alkylation of 5-R-1H-tetrazoles with available allylcarboranes. Abstract: An efficient triflic acid catalyzed regioselective alkylation of 5-R-1H-tetrazoles with readily available allylcarboranes is reported. The suggested synthetic procedure allows the formation of a variety of carboranyl-substituted tetrazoles in a good yield under mild conditions. Transformations of newly synthesized carboranyl tetrazoles under UV irradiation were studied. Allylcarboranes as starting materials were prepared via Pd-catalyzed cross-coupling reaction of iodocarboranes with allylmagnesium bromide.