학술논문
Reversible Boron-Insertion into Aromatic C-C Bonds.
Document Type
Academic Journal
Author
Kuroki K; Department of Chemistry, School of Science, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.; Ito T; Department of Chemistry, School of Science, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.; Takaya J; Department of Chemistry, School of Science, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
Source
Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: PubMed not MEDLINE; MEDLINE
Subject
Language
English
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.
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)