Ruthenium-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes and Selenocyanates: An Entry to Selenopyridine Derivatives

Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

A novel synthetic method for the preparation of selenopyridine derivatives, involving a [2+2+2] cycloaddition of α,ω-diynes and selenocyanates that is catalyzed by a ruthenium complex is described. This mild and straightforward reaction allows access to a wide range of selenopyridines with high yields and excellent regioselectivities, using dichloromethane or dichloroethane as solvents, at either 50 or 80 °C. Post-functionalization of halogenated cycloadducts via cyanation using copper and S_NAr reaction provides substituted selenopyridines with good yields.

Key words

ruthenium - cycloaddition - selenium - heterocycles - pyridines

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