An Inorganic Huisgen Reaction between a 1,2‐Diboraallene and an Azide to Access a Diboratriazole

Regioselective Huisgen cycloaddition reaction between 1,2‐diboraallene and azide proceeds under catalyst‐free and mild conditions to furnish a diboratriazole (2). X‐ray diffraction analysis and computational studies confirmed the delocalization of π electrons over the B2N3 five‐membered ring of (2),...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-10, Vol.61 (42), p.e202207631-n/a
Main Authors: Zhu, Lizhao, Kinjo, Rei
Format: Article
Language:English
Subjects:
Aromaticity
azides
Boron
Catalysts
Computer applications
Cycloaddition
cycloaddition reactions
Density functional theory
Huisgen Reaction
regioselectivity
Triazole
X-ray diffraction
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Summary:Regioselective Huisgen cycloaddition reaction between 1,2‐diboraallene and azide proceeds under catalyst‐free and mild conditions to furnish a diboratriazole (2). X‐ray diffraction analysis and computational studies confirmed the delocalization of π electrons over the B2N3 five‐membered ring of (2), indicating its aromatic features. Molecule (2) spontaneously releases N2 to form the 2,3‐dibora‐4‐aza‐1,3‐butenyne derivative (3). The mechanism of a whole reaction profile was extensively investigated by density functional theory (DFT) calculations. This work demonstrates that the regioselective cycloaddition of 1,2‐diboraallene with aryl azide, namely, Huisgen 1,3‐dipolar cycloaddition, affords an aromatic diboratriazole derivative. The diboratriazole readily releases N2 without the aid of any catalysts to furnish a 2,3‐dibora‐4‐aza‐1,3‐butenyne derivative.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202207631