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Reversible Photoisomerization from Borepin to Boratanorcaradiene and Double Aryl Migration from Boron to Carbon
Author(s) -
He ZheChang,
Mellerup Soren K.,
Liu Lijie,
Wang Xiang,
Dao Caitlin,
Wang Suning
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201902231
Subject(s) - photoisomerization , chemistry , aryl , isomerization , moiety , steric effects , photochemistry , dimer , boron , pyridine , carbon atom , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
Abstract B(npy)Ar 2 (npy=2‐(naphthalen‐1‐yl)pyridine) compounds bearing various nonbulky aryl groups undergo a clean and sequential two‐step photoisomerization in which two aryl substituents on boron migrate to a carbon atom of the naphthyl moiety. The second isomerization step is the first example of a reversible photoisoermization between a borepin and a borirane. Both steric and electronic factors have been found to have a great impact on this photoreactivity. Furthermore, the borirane isomer reacts with oxygen, forming a rare oxaborepin dimer.