Reversible Boron‐Insertion into Aromatic C−C Bonds

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Abstract: Formation of borabicyclo[3.2.0]heptadiene derivatives was achieved via boron‐insertion into aromatic C−C bonds in the photo‐promoted skeletal rearrangement reaction of triarylboranes bearing an ortho‐phosphino substituent (ambiphilic phosphine‐boranes). The borabicyclo[3.2.0]heptadiene derivatives were fully characterized by NMR and X‐ray analyses. The dearomatized products were demonstrated to undergo the reverse reaction in the dark at room temperature, realizing photochemical and thermal interconversion between triarylboranes and boron‐doped bicyclic systems. Experimental and theoretical studies revealed that sequential two electrocyclic reactions involving E/Z‐isomerization of an alkene moiety proceed via a highly strained trans‐borepin intermediate.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Reversible Boron‐Insertion into Aromatic C−C Bonds ; day:09 ; month:10 ; year:2023 ; extent:7
Angewandte Chemie / International edition. International edition ; (09.10.2023) (gesamt 7)

Creator: Kuroki, Kaito
Ito, Tatsuyoshi
Takaya, Jun

DOI: 10.1002/anie.202312980

URN: urn:nbn:de:101:1-2023101015131894883000

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:02 AM CEST

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Kuroki, Kaito
Ito, Tatsuyoshi
Takaya, Jun

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