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

Synthesis - Tập 51 Số 12 - Trang 2532-2541 - 2019
Christine Tran1, Mansour Haddad1, Virginie Ratovelomanana‐Vidal2
1Institute of Chemistry for Life and Health Sciences
2PSL Research University, Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences

Tóm tắt

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 SNAr reaction provides substituted selenopyridines with good yields.

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