Polarity-Driven Thiyl\nRadical-Catalyzed Aerobic Debenzylation\nof Ethers and Amines

We report the use\nof a strongly electrophilic thiyl radical derived\nfrom commercially available pentafluorothiophenol as a demonstration\nof highly chemoselective H atom abstraction from electron-rich and\nrelatively weak benzylic C–H bonds adjacent to the O and N\natoms. This approach enables the selective oxidative removal of benzyl\nand <i>p</i>-methoxybenzyl groups from amines and ethers\nunder ambient aerobic conditions.

Publication Details

Journal
Figshare
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.joc.4c01796.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Polarity-Driven Thiyl\nRadical-Catalyzed Aerobic Debenzylation\nof Ethers and Amines

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Catalytic C–H Functionalization Methods
article

Polarity-Driven Thiyl\nRadical-Catalyzed Aerobic Debenzylation\nof Ethers and Amines

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Abstract

We report the use\nof a strongly electrophilic thiyl radical derived\nfrom commercially available pentafluorothiophenol as a demonstration\nof highly chemoselective H atom abstraction from electron-rich and\nrelatively weak benzylic C–H bonds adjacent to the O and N\natoms. This approach enables the selective oxidative removal of benzyl\nand <i>p</i>-methoxybenzyl groups from amines and ethers\nunder ambient aerobic conditions.

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Catalytic C–H Functionalization Methods
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Polarity-Driven Thiyl\nRadical-Catalyzed Aerobic Debenzylation\nof Ethers and Amines · Figshare (2024) | TGRS Research Map | TGRS