Metal-free aminofluorination of α-diazo 2H-benzopyran-4-one: convenient access to β-fluoramides

We have developed a convenient synthesis of a series of β-fluoramides in 65% yield. The process involved a tandem fluorination/Ritter reaction to synthesize β-fluoramides using α-diazo 2H-benzopyran-4-one compounds. Selectfluor was used as the electrophilic fluoride source in acetonitrile to build t...

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Published inOrganic & biomolecular chemistry Vol. 20; no. 35; pp. 7027 - 7030
Main Authors Zhang, Wentao, Sun, Minghao, You, Kejia, Pang, Yunfei, Ma, Baochun
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 11.08.2022
Subjects
Acetonitrile
Chemical reactions
Chemical synthesis
Fluorides
Fluorination
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Summary:We have developed a convenient synthesis of a series of β-fluoramides in 65% yield. The process involved a tandem fluorination/Ritter reaction to synthesize β-fluoramides using α-diazo 2H-benzopyran-4-one compounds. Selectfluor was used as the electrophilic fluoride source in acetonitrile to build the β-fluorinated quaternary carbon center and amide derivatives of 2H-benzopyran-4-one in one step. The products N-(2-(2-fluoro-2,3-dihydro-3-oxobenzofuran-2-yl)propan-2-yl)acetamides were a series of bifunctional compounds with a 2-fluoro-2,3-dihydro-3-oxobenzofuran motif and amide groups.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01089e