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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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Supplementary files

Article information


Submitted
22 Mar 2016
Accepted
12 May 2016
First published
13 May 2016

Org. Chem. Front., 2016,3, 875-879
Article type
Research Article

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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