Nickel-Catalyzed Hydroalkenylation of Alkynes through C–F Bond Activation: Synthesis of 2-Fluoro-1,3-dienes

Published as part of the Special Topic Advanced Strategies in Synthesis with Nickel

Abstract

2-Fluoro-1,3-dienes were synthesized through nickel-catalyzed coupling reactions between β,β-difluorostyrenes and alkynes in the presence of ZrF₄ as co-catalyst and a hydride source derived from triethylborane and lithium isopropoxide. Mechanistic studies revealed that the carbon–fluorine bond was cleaved by β-fluorine elimination from intermediary nickelacyclopentenes generated through oxidative cyclization of the two substrates.

Key words

C–F bond activation - nickel - hydroalkenylation - β-fluorine elimination - oxidative cyclization - 1,3-dienes - fluorine - alkynes

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