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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(CH₃ )₃ , F, Cl) by a BN-Aryne.

ABSTRACT: 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.

SUBMITTER: Keck C

PROVIDER: S-EPMC9299606 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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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(CH3 )3 , F, Cl) by a BN-Aryne.

Keck Constanze C Hahn Jennifer J Gupta Divanshu D Bettinger Holger F HF

Chemistry (Weinheim an der Bergstrasse, Germany) 20211202 5

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 tha ...[more]

PMID: 34854508

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