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

Ravindra S. Phatake; Tizian Müller; Arthur Averdunk; Urs Gellrich

doi:10.1039/d2qo01998a

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

Ravindra S. Phatake
, Tizian Müller
, Arthur Averdunk
, Urs Gellrich

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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.

Original language	English
Pages (from-to)	1128-1133
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	10
Issue number	5
DOIs	https://doi.org/10.1039/d2qo01998a
State	Published - 24 Jan 2023
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "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.",

author = "Phatake, \{Ravindra S.\} and Tizian M{\"u}ller and Arthur Averdunk and Urs Gellrich",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

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doi = "10.1039/d2qo01998a",

language = "English",

volume = "10",

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journal = "Organic Chemistry Frontiers",

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TY - JOUR

T1 - Bis(pentafluorophenyl)borane-catalyzed E-selective isomerization of terminal alkenes to internal alkenes

AU - Phatake, Ravindra S.

AU - Müller, Tizian

AU - Averdunk, Arthur

AU - Gellrich, Urs

PY - 2023/1/24

Y1 - 2023/1/24

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85147413881

U2 - 10.1039/d2qo01998a

DO - 10.1039/d2qo01998a

M3 - Article

AN - SCOPUS:85147413881

SN - 2052-4110

VL - 10

SP - 1128

EP - 1133

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 5

ER -

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

Abstract

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