Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 3, Issue 7, Pages 875-879Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00109b
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Funding
- Department of Science and Technology of Shaanxi Province [2015KJXX-02]
- National Science Foundation of China [21472146]
- Research Grants Council of Hong Kong [HKUST 603313]
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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.
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