Synthesis 2019; 51(12): 2532-2541
DOI: 10.1055/s-0037-1610704
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Christine Tran
,
Mansour Haddad
,
PSL Research University, Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences, 11 rue Pierre et Marie Curie, Paris, 75005, France   Email: virginie.vidal@chimie-paristech.fr
› Author Affiliations
Further Information

Publication History

Received: 13 March 2019

Accepted after revision: 14 March 2019

Publication Date:
10 April 2019 (eFirst)

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 SNAr reaction provides substituted selenopyridines with good yields.

Supporting Information

 
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