4.5 Article

3-Trifloxy-3-(trifluoromethyl)prop-2-ene 1-Iminium Salts as Precursors for Elusive 3-(Trifluoromethyl)prop-2-yne 1-Iminium Salts

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2021, 期 23, 页码 3426-3441

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100567

关键词

Alkynes; Cycloaddition; Iminium Salts; Organofluorine Compounds; 1; 2; 3-Triazoles

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3-(Trifluoromethyl)prop-2-yne 1-iminium triflate salts were synthesized by elimination of triflic acid, and exhibited excellent reactivity in various cycloaddition reactions.
Abstract: 3-(Trifluoromethyl)prop-2-yne 1-iminium triflate salts were generated from 3-trifloxy-3-(trifluoromethyl)prop-2-ene 1-iminium salts by triethylamine-assisted elimination of triflic acid and trapped in situ in various cycloaddition reactions. These included Diels-Alder reactions with 1,3-dienes, [2+2] cycloaddition with 1,4-diphenylbuta-1,3-diene, and [3+2] cycloaddition with organoazides. All these reactions revealed the excellent dienophilic and dipolarophilic reactivity of the electrophilic C,C triple bond of the novel 3-CF3-propyniminium salts.

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