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Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si‐E Single Bonds (E=H, OSi(CH 3 ) 3 , F, Cl) by a BN‐Aryne
Author(s) -
Keck Constanze,
Hahn Jennifer,
Gupta Divanshu,
Bettinger Holger F.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103614
Subject(s) - boron , aryne , chemistry , reactivity (psychology) , nitrogen , silicon , crystallography , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , medicine , alternative medicine , pathology
The boron‐nitrogen analogue of ortho ‐benzyne, 1,2‐azaborinine, is a reactive intermediate that features a formal boron‐nitrogen triple bond. We here show by combining experimental and computational techniques that the Lewis acidity of the boron center of dibenzo[c,e][1,2]azaborinine allows interaction with the silicon containing single bonds Si−E through the silicon bonding partner E (E=F, Cl, OR, H). The binding to boron activates the Si−E bonds for subsequent insertion reaction. This shows that the BN‐aryne is a ferocious species that even can activate and insert into the very strong Si−F bond.