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Semiconductor photocatalyst helps to realize borylation reaction

Semiconductor photocatalyst helps to realize borylation reaction
Credit: Angewandte Chemie International Edition (2023). DOI: 10.1002/anie.202306846

A research group led by Prof. Dai Wen from the Dalian Institute of Chemical Physics (DICP) of the Chinese Academy of Sciences (CAS) has realized borylation reactions involving N-heterocyclic carbene boranes (NHC-BH3) with a simple and efficient heterogeneous photocatalytic system, enabling synthesis of high-value transformations including hydroboration and boron substitution products. Their study was published in Angewandte Chemie International Edition on Aug. 9.

NHC-BH3 are novel boron sources in free radical borylation reactions due to their stable chemical properties and straightforward preparation method. However, the application of NHC-BH3 is hindered by the requirement of a large quantity of harmful free radical initiators, as well as the expensive and non-recyclable homogeneous photocatalysts.

For this study, the researchers used cadmium sulfide nanosheets, which were easily prepared, as heterogeneous photocatalysts. And they served NHC-BH3 as a boron source, enabling the selective borylation reaction of various alkenes, alkynes, imines, aromatic (hetero) rings, and bioactive molecules under and . Since the fully utilized photogenerated electron-hole pairs, the need for sacrificial agents was eliminated.

Furthermore, they found that the photocatalytic system could not only achieve gram-scale scale-up, but also maintain a stable yield after multiple cycles of the catalyst. It could also serve as a recyclable general platform, allowing the recovered catalyst to continue catalyzing different kinds of substrates.

"Our study provide new ideas for the development of free radical borylation reactions using NHC-BH3 as a boron source, and the organoboranes obtained from the reaction may be used to synthesize synthetic building blocks that contain , borate, and difluoroborane reactive sites," said Prof. Dai.

More information: Fukai Xie et al, Facile Borylation of Alkenes, Alkynes, Imines, Arenes and Heteroarenes with N‐Heterocyclic Carbene‐Boranes and a Heterogeneous Semiconductor Photocatalyst, Angewandte Chemie International Edition (2023). DOI: 10.1002/anie.202306846

Citation: Semiconductor photocatalyst helps to realize borylation reaction (2023, August 30) retrieved 28 November 2023 from
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