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Issue 24, 2018
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Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage

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Abstract

Unprecedented quadruple cleavage of halodifluoromethyl compounds has been disclosed for the first time, resulting in carbonyl synthons for reaction with various amines. Mechanistic studies suggested that difluorocarbenes were first formed in situ between amines and halodifluoromethyl compounds, and further double C(sp3)–F bond cleavage occurred under basic conditions, resulting in valuable formamides. Late stage modifications were successfully employed on various medicinal drugs.

Graphical abstract: Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage

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Publication details

The article was received on 17 Jul 2018, accepted on 23 Sep 2018 and first published on 25 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00727F
Citation: Org. Chem. Front., 2018,5, 3505-3509

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    Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage

    X. Ma, S. Deng and Q. Song, Org. Chem. Front., 2018, 5, 3505
    DOI: 10.1039/C8QO00727F

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