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DOI: 10.1055/s-0036-1588447
A Three-Component Reaction for the One-Pot Preparation of β-Amino-α,α-Difluoroketones from Trimethyl(trifluoromethyl)silane (CF3TMS), Acylsilanes and Imines
Publication History
Received: 11 April 2017
Accepted after revision: 05 May 2017
Publication Date:
13 June 2017 (online)
Abstract
A methodology allowing the direct preparation of β-amino-α,α-difluoroketones from the Ruppert–Prakash reagent (CF3TMS), acyltrimethylsilanes and N-Boc or N-(diphenylphosphinyl)imines is reported. The process, initiated by a catalytic amount of tetra-n-butylammonium difluorotriphenylsilicate (TBAT), involves the addition of CF3TMS to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion. The latter promotes the addition of the resulting difluoroenoxysilane to the imine. The higher electrophilicity of the acylsilane compared to the imine allows the direct mixing of all the reagents in a three-component, one-pot process.
Key words
Mannich reactions - fluorine - tandem reaction - multicomponent reaction - Ruppert–Prakash reagentSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588447.
- Supporting Information
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