1449689-92-2Relevant articles and documents
Electrophilic Cyanative Alkenylation of Arenes
Zhao, Mingyue,Barrado, Alejandro G.,Sprenger, Kristin,Golz, Christopher,Mata, Ricardo A.,Alcarazo, Manuel
, p. 4932 - 4937 (2020)
A variety of appropriately substituted internal alkynes were transformed into the corresponding cyano-substituted phenanthrenes, dihydronaphthalenes, and cyclohepta-1,3,5-trienes in moderate to excellent yields by treatment with imidazolium thiocyanate 1, which serves as an easy to handle [CN]+ precursor, in the presence of BCl3. The synthetic value of the method is additionally demonstrated by the transformation of the primarily obtained products into heavily substituted quinolines. Additionally, the dynamic properties of the prepared dibenzocyclohepta-1,3,5-trienes have been investigated.
Calcium-catalyzed carboarylation of alkynes
Fu, Liang,Niggemann, Meike
supporting information, p. 6367 - 6370 (2015/04/22)
The first transition-metal-free carboarylation of alkynes with commercial and readily available alcohols as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, is provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple experimental operation under mild reaction conditions. Finally free: The first transition-metal-free one-step synthesis of highly congested, all-carbon tetrasubstituted olefins has been realized by a calcium-catalyzed carboarylation reaction. Internal alkynes react with alcohols as alkylating reagent under mild reaction conditions, which provides access to a variety of useful structural scaffolds via highly reactive trisubstituted vinyl cations.
Copper-catalyzed carboarylation of alkynes via vinyl cations
Walkinshaw, Andrew J.,Xu, Wenshu,Suero, Marcos G.,Gaunt, Matthew J.
supporting information, p. 12532 - 12535 (2013/09/23)
Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.
