Journal
GREEN CHEMISTRY
Volume 24, Issue 8, Pages 3293-3299Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc00310d
Keywords
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Funding
- National Natural Science Foundation of China [21871226, 22071211]
- Science and Technology Planning Project of Hunan Province [2019RS2039]
- Hunan Provincial Natural Science Foundation of China [2020JJ3032]
- Open Research Fund of School of Chemistry and Chemical Engineering of Henan Normal University [2022C02]
- Postgraduate Scientific Research Innovation Project of Hunan Province [XDCX2021B156]
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A visible-light/nickel dual catalyzed stoichiometric coupling of methylarenes via bromine radical-enhanced HAT has been developed, demonstrating high synthetic utility in late-stage arylation or benzylation of drug-like and complex molecules.
A visible-light/nickel dual catalyzed stoichiometric coupling of methylarenes via bromine radical-enhanced HAT has been developed. Aryl bromides serve as both cross-coupling partners and bromine radical precursors. Mechanistic studies reveal that the bromine radical acts as a highly efficient HAT reagent to abstract the benzylic C(sp(3))-H bond to deliver a benzylic radical and subsequently engages in Ni-catalyzed arylation couplings. The synthetic utility of this approach is further proved by its application in the late-stage arylation or benzylation of several drug-like and complex molecules in a stoichiometric manner.
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