Bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes

We report the bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes. The reaction proceeds under comparatively mild conditions and requires only low catalyst loadings. Notably, a long-range isomerization of distant aryl alkenes is possible with the protocol reported herein. The mechanism was investigated by dispersion-corrected spin-component scaled double hybrid DFT computations, which indicate that the bis(pentafluorophenyl)borane catalyzed alkene isomerization proceeds via a hydroboration/retro-hydroboration sequence.

Automated summary

We have discovered a bis(pentafluorophenyl)borane-catalyzed isomerization reaction that selectively converts terminal alkenes to internal alkenes. This transformation can be achieved under mild reaction conditions and with low catalyst loadings. Interestingly, our method also allows for long-range isomerization of aryl alkenes. We have investigated the reaction mechanism using dispersion-corrected spin-component scaled double hybrid DFT computations, revealing a hydroboration/retro-hydroboration sequence.