Direct Alkylarene Desaturation via Base-Promoted Halogen Transfer

Abstract

We report a method to prepare alkenes through the base-promoted oxidative desaturation of alkylarenes and related weakly acidic functional groups. This process operates via a tandem deprotonative-halogenation and elimination sequence using haloarene halogen-transfer reagents. The use of potassium tert-butoxide with haloarene oxidants provides a simple means to desaturate a broad range of alkylarenes, acids, esters, and amides, as well as to aromatize saturated heterocycles. A critical feature for reaction success is the generation of tert-butanol from the tert-butoxide base which buffers the reaction solution to prevent anionic alkene polymerization. The utility of this approach is enhanced by its direct sequencing with additional base-promoted processes, such as hydrofunctionalization, to access formal homobenzylic C–H functionalization products.

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BibTeX RIS

BibTeX

@misc{sugg2026direct,
  title = {{Direct Alkylarene Desaturation via Base-Promoted Halogen Transfer}},
  author = {Eve L. Sugg and Garrett A. Hoteling and Viet Ngo and Jeffrey S. Bandar},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15009162/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009162/v1},
  note = {CC BY-NC-ND},
}

RIS

TY  - UNPB
TI  - Direct Alkylarene Desaturation via Base-Promoted Halogen Transfer
AU  - Eve L. Sugg
AU  - Garrett A. Hoteling
AU  - Viet Ngo
AU  - Jeffrey S. Bandar
PY  - 2026
DA  - 2026/09/21
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009162/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009162/v1
AB  - We report a method to prepare alkenes through the base-promoted oxidative desaturation of alkylarenes and related weakly acidic functional groups. This process operates via a tandem deprotonative-halogenation and elimination sequence using haloarene halogen-transfer reagents. The use of potassium tert-butoxide with haloarene oxidants provides a simple means to desaturate a broad range of alkylarenes, acids, esters, and amides, as well as to aromatize saturated heterocycles. A critical feature for reaction success is the generation of tert-butanol from the tert-butoxide base which buffers the reaction solution to prevent anionic alkene polymerization. The utility of this approach is enhanced by its direct sequencing with additional base-promoted processes, such as hydrofunctionalization, to access formal homobenzylic C–H functionalization products.
ER  -

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