Radical-mediated carboselenation of terminal alkynes under mild conditions

Abstract

A direct carboselenation of terminal alkynes with diorganyl diselenides and azobisisoalkylcarbonitriles via a radical process has been disclosed, affording the corresponding (E)-γ-seleno-substituted allyl nitriles with excellent regioselectivity and stereoselectivity. This method features catalyst- and additive-free conditions, less toxic cyanating sources, readily available reagents and broad substrate generality. Additionally, the practicability of this reaction and its reaction mechanism are demonstrated.