β-Functionalized and α,β-Difunctionalized Ketones from 1-Arylallylic Alcohols via Dipotassio α,β-Dianion Intermediates

26 August 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

This study reports the synthesis of diverse β-functionalized ketones from readily available 1-arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α,β-dianion as the key intermediate, which served as a metal homoenolate equivalent. This protocol also allowed the one-pot synthesis of α,β-difunctionalized ketones using two different electrophiles, thus demonstrating its synthetic advantages over other protocols involving metal homoenolates.

Keywords

potassium
dianions
homoenolates
enolates
ketones

Supplementary materials

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Supporting Information
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General information, experimental procedures, characterization data, computational study, and NMR spectra.
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