Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 28, Pages 15243-15247Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202102313
Keywords
benzylic oxidation; catalysis; copper; electron paramagnetic resonance; metal-organic framework
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Funding
- EPSRC [EP/I011870]
- Royal Society
- University of Manchester
- EPSRC
- European Research Council (ERC) under the European Union [742401]
- Royal Society Newton International Fellowships
- European Research Council (ERC) [742401] Funding Source: European Research Council (ERC)
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This study presents an efficient method for oxidizing benzylic C-H groups using the metal-organic framework material MFM-170, which can be applied to a wide range of substrates under mild conditions. Comprehensive investigations utilizing electron paramagnetic resonance (EPR) spectroscopy and synchrotron X-ray diffraction have identified the critical role of the paddlewheel moiety in activating the oxidant.
Selective oxidation of benzylic C-H compounds to ketones is important for the production of a wide range of fine chemicals, and is often achieved using toxic or precious metal catalysts. Herein, we report the efficient oxidation of benzylic C-H groups in a broad range of substrates under mild conditions over a robust metal-organic framework material, MFM-170, incorporating redox-active [Cu-2(II)(O2CR)(4)] paddlewheel nodes. A comprehensive investigation employing electron paramagnetic resonance (EPR) spectroscopy and synchrotron X-ray diffraction has identified the critical role of the paddlewheel moiety in activating the oxidant (BuOOH)-Bu-t (tert-butyl hydroperoxide) via partial reduction to [(CuCuI)-Cu-II(O2CR)(4)] species.
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