Gold-Catalyzed Synthesis of Tetrazoles from Alkynes by C=C Bond Cleavage**
نویسندگان
چکیده
Cycloadditions of azides with alkynes to form triazoles under thermal conditions (Huisgen cycloaddition) or in the presence of copper [click reaction, copper-catalyzed azide– alkyne cycloaddition (CuAAC)] are reactions of fundamental importance in organic chemistry. Triazoles can also be obtained by means of ruthenium, silver, and iridium catalysis, as well as by a zinc-mediated process. In sharp contrast, very different reactivity has been observed in the reaction of terminal alkynes with TMSN3 in the presence of group 11 metal salts and complexes. Thus, the group of Jiao recently made the remarkable observation that alkynes (1; R= alkyl, aryl, alkenyl) react with TMSN3 in the presence of Ag2CO3 as catalyst to form nitriles (2 ; Scheme 1). [9] The same
منابع مشابه
Au-catalyzed tandem cyclization/[1,2]-alkyl migration reaction of epoxy alkynes: synthesis of spiropyranones.
A novel gold-catalyzed tandem cyclization/[1,2]-alkyl migration process of epoxy alkynes to spiropyranones has been discovered. From this process, the construction of adjacent multiple stereocenters with a new quaternary carbon atom is achieved. The gold-catalyzed domino process is stereospecific with respect to the migrating carbon atom. A type of unusual C-C bond cleavage of epoxide systems h...
متن کاملFacile synthesis of 5-substituted-1H-tetrazoles catalyzed by reusable nickel zirconium phosphate nanocatalyst
5-Substituted-1H-tetrazoles were synthesized by the [3 + 2] cycloaddition of sodium azide with various nitriles in the presence of nickel zirconium phosphate (NiZrP) as an effective heterogeneous catalyst in dimethylsulfoxide at 120 °C. This method has the advantages of good to high yields, simple methodology and easy work-up. The catalyst can be recovered by centrifuging and reused with good y...
متن کاملRhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation.
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford the corresponding products in moderate to excellent yields.
متن کاملTransition metal-catalyzed carbon-carbon bond activation.
This tutorial review deals with recent developments in the activation of C-C bonds in organic molecules that have been catalyzed by transition metal complexes. Many chemists have devised a variety of strategies for C-C bond activation and significant progress has been made in this field over the past few decades. However, there remain only a few examples of the catalytic activation of C-C bonds...
متن کامل