Beilstein J. Org. Chem.2025,21, 458–472, doi:10.3762/bjoc.21.33
improve the result. However, the addition of a LAG agent (MeOH, 50 μL) in the automatedgrinding step dramatically improved the outcome (quantitative conversion after 20 h of irradiation). Intriguingly, the simultaneous LAVG and irradiation enabled the formation of 5.3 in 97% yield upon reduced
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Graphical Abstract
Figure 1:
The Grotthuss–Draper, Einstein–Stark, and Beer–Lambert laws. T: transmittance; ε: molar attenuation...
Beilstein J. Org. Chem.2022,18, 999–1008, doi:10.3762/bjoc.18.100
reaction time, and mild reaction conditions are a few noticeable merits of this environmentally sustainable mechanochemical protocol.
Keywords: automatedgrinding; chemoselectivity; mechanochemistry; N-bromosuccinimide; PEG-400; regioselectivity; stoichiometry-controlled halogenation; Introduction
Aryl
aniline derivatives also worked well to afford the desired products in high yields (products 2u and 3j in Scheme 4). In all cases, no prominent substituent effect was observed in terms of yields and reaction time.
Next, we planned to further diversify this halogenation protocol via automatedgrinding for
Representative examples of important halogen-containing aryl derivatives.
Strategies for halogenation of aromatic compounds using NXS.
General scheme of PEG-400-assisted halogenation of phenols and anilines in an automated grinder using NXS.
Monohalogenation of phenols and anilines by automatedgrinding with NXS
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Graphical Abstract
Figure 1:
Representative examples of important halogen-containing aryl derivatives.