Catalyst‐Free Diborylation and Silaboration of Azoarenes: A Simple Photoinduced Approach

The diborylation of the N=N double bond of azoarenes has been achieved using a commercially available diboron reagent, B2cat2 [bis(catecholato)diboron]. By utilizing the photo‐switchable nature of azoarenes under blue‐LED light irradiation, an uncatalyzed diborylation and silaboration yielded a broa...

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Veröffentlicht in:Angewandte Chemie International Edition 2025-01, Vol.64 (3), p.e202415913-n/a
Hauptverfasser: Mondal, Reetu Rani, Pal, Apurba Kumar, Geetharani, K.
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Sprache:eng
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Zusammenfassung:The diborylation of the N=N double bond of azoarenes has been achieved using a commercially available diboron reagent, B2cat2 [bis(catecholato)diboron]. By utilizing the photo‐switchable nature of azoarenes under blue‐LED light irradiation, an uncatalyzed diborylation and silaboration yielded a broad range of functionalized hydrazine derivatives. The mechanistic origin validates the importance of cis configuration, which is corroborated by theoretical calculations. We have shown that, in the absence of a catalyst or a base, azoarenes′ photoswitchability can be exploited to aid in their diborylation into 1,2‐bis(boryl)hydrazines. The transformation is achieved using commercially available diboron reagent, bis(catecholato)diboron and extremely mild conditions are used in the devised approach. Moreover, silaboranes were also activated using this process to yield 1‐silyl‐2‐borylhydrazines.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202415913