Issue 5, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
16 Dec. 2022
Accepted
21 Janv. 2023
First published
24 Janv. 2023

Org. Chem. Front., 2023,10, 1128-1133

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

R. S. Phatake, T. Müller, A. Averdunk and U. Gellrich, Org. Chem. Front., 2023, 10, 1128 DOI: 10.1039/D2QO01998A

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