Selective Oxyfunctionalization\nof Benzylic C–H\nwith No Solvent

The direct selective oxyfunctionalization\nof C–H\ninto CO\nrepresents a highly useful, yet challenging, synthetic methodology.\nHerein, a one-step oxyfunctionalization of benzylic C–H into\naryl ketone, with no overoxidation of the −OH functional group,\nis reported through mechanochemistry. The substrate scope is also\ntolerant of a wide range of different functional groups, providing\na particularly sustainable yet widely adaptable route for the synthesis\nof aryl ketones, which represent both a classic synthetic precursor\nand a useful strategy for lignin monomer valorization. A series of\nmechanistic and spectroscopic investigations were also conducted to\nshed light on the unique C–H over −OH selectivity, opening\nup new avenues for oxidation chemistry.

Publication Details

Journal
Figshare
Published
2024-11-06
DOI
https://doi.org/10.1021/acs.joc.4c01950.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Selective Oxyfunctionalization\nof Benzylic C–H\nwith No Solvent

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Catalytic C–H Functionalization Methods
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Selective Oxyfunctionalization\nof Benzylic C–H\nwith No Solvent

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Abstract

The direct selective oxyfunctionalization\nof C–H\ninto CO\nrepresents a highly useful, yet challenging, synthetic methodology.\nHerein, a one-step oxyfunctionalization of benzylic C–H into\naryl ketone, with no overoxidation of the −OH functional group,\nis reported through mechanochemistry. The substrate scope is also\ntolerant of a wide range of different functional groups, providing\na particularly sustainable yet widely adaptable route for the synthesis\nof aryl ketones, which represent both a classic synthetic precursor\nand a useful strategy for lignin monomer valorization. A series of\nmechanistic and spectroscopic investigations were also conducted to\nshed light on the unique C–H over −OH selectivity, opening\nup new avenues for oxidation chemistry.

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Catalytic C–H Functionalization Methods
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Selective Oxyfunctionalization\nof Benzylic C–H\nwith No Solvent · Figshare (2024) | TGRS Research Map | TGRS