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Issue 7, 2016
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Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions

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Abstract

A metal-free borylation reaction of electron-rich aryl chlorides, fluorides, mesylates and phosphates under continuous-flow photolytic conditions is reported. The flow setup was designed to facilitate this process efficiently in comparison with the batch mode. Owing to its unique chemical selectivity, mild reaction conditions, good functional group tolerance and substrate scope, this reaction adds a complementary protocol to the current synthetic methods for boronic acid derivatives. The proposed reaction mechanism involves a photolytically generated triplet aryl cation, and DFT calculations suggest that the borylation product is formed in an anion-mediated single step process passing a minimum energy crossing point.

Graphical abstract: Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions

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Publication details

The article was received on 22 Mar 2016, accepted on 12 May 2016 and first published on 13 May 2016


Article type: Research Article
DOI: 10.1039/C6QO00109B
Citation: Org. Chem. Front., 2016,3, 875-879
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    Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions

    K. Chen, M. S. Cheung, Z. Lin and P. Li, Org. Chem. Front., 2016, 3, 875
    DOI: 10.1039/C6QO00109B

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