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Synthesis
DOI: 10.1055/s-0043-1775416
DOI: 10.1055/s-0043-1775416
paper
Boryl Radical Chemistry
B2(OH)4 and Et3N-BH3: A New Combination of Reagents for the Mild and Efficient Photoreduction of Nitro(hetero)arenes
B.R. thanks Janssen Pharmaceutica for a PhD CASE Award.
Abstract
Anilines are a common motif in many bioactive compounds and their production through the reduction of nitroarenes has become an essential method for their synthesis. We demonstrate that the combination of an amine-borane complex and hypoboric acid (tetrahydroxydiborane) under visible light irradiation can accomplish the reduction of nitroarenes to the corresponding anilines. Preliminary mechanistic studies suggest the generation of boryl radicals via a hydrogen atom transfer (HAT) step from the photoexcited nitroarene. Involvement of a parallel thermal pathway is demonstrated with the high reaction efficiency being partially attributed to both routes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775416.
- Supporting Information
Publication History
Received: 30 September 2024
Accepted after revision: 21 October 2024
Article published online:
11 November 2024
© 2024. Thieme. All rights reserved
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