Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 10, Pages 1491-1495Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900411
Keywords
Chlorination; Photoredox catalysis; Oxidation; ipso-Substitution; Green chemistry
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Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.
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