Bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes. Issue 5 (30th January 2023)

• Record Type: Journal Article
• Authors: Phatake, Ravindra S.; Müller, Tizian; Averdunk, Arthur; Gellrich, Urs
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 5(2023)
• Page Start: 1128
• Page End: 1133
• Publication Date: 2023-01-30
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01998a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The bis(pentafluorophenyl)borane-catalyzed E -selective isomerization of terminal alkenes to internal alkenes via a hydroboration/retro-hydroboration sequence is reported. 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.