Formal Dearomative\nHydroamination of 2‑Arylphenols

An acid-promoted dearomative rearrangement of <i>O</i>-arylhydroxylamines affords 2-aminocyclohexadien-1-ones,\nwhich can\nin turn be reductively quenched for the synthesis of <i>trans</i>-aminoalcohols on a cyclohexadiene core. This method serves as an\nefficient entry to the pharmaceutically relevant 1-arylcyclohexylamine\nscaffold in two steps (one purification) from commercially available\nor readily prepared 2-arylphenols.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/acs.joc.4c02654.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Formal Dearomative\nHydroamination of 2‑Arylphenols

Figshare
Catalytic C–H Functionalization Methods
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Formal Dearomative\nHydroamination of 2‑Arylphenols

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Abstract

An acid-promoted dearomative rearrangement of <i>O</i>-arylhydroxylamines affords 2-aminocyclohexadien-1-ones,\nwhich can\nin turn be reductively quenched for the synthesis of <i>trans</i>-aminoalcohols on a cyclohexadiene core. This method serves as an\nefficient entry to the pharmaceutically relevant 1-arylcyclohexylamine\nscaffold in two steps (one purification) from commercially available\nor readily prepared 2-arylphenols.

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Catalytic C–H Functionalization Methods
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Formal Dearomative\nHydroamination of 2‑Arylphenols · Figshare (2024) | TGRS Research Map | TGRS