Synthesis of\nPentafluorosulfanylated Ynamides\nand Further Functionalizations

Herein is described the first synthesis of SF<sub>5</sub>-ynamides,\nversatile building blocks featuring the pentafluorosulfanyl motif.\nThis synthesis proceeds through a two-step sequence of radical SF<sub>5</sub>-addition onto the π-system of a wide range of terminal\nynamides and derivatives substituted with various nitrogen fragments\nfollowed by a dehydrochlorination reaction. A selection of downstream\nfunctionalization reactions, including nucleophilic additions, cycloadditions,\nand sulfur ylide synthesis, highlights the wide-ranging applications\nof this novel type of functionalized SF<sub>5</sub>-building block.

Publication Details

Journal
Figshare
Published
2024-11-26
DOI
https://doi.org/10.1021/acs.orglett.4c03972.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Synthesis of\nPentafluorosulfanylated Ynamides\nand Further Functionalizations

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Fluorine in Organic Chemistry
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Synthesis of\nPentafluorosulfanylated Ynamides\nand Further Functionalizations

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Abstract

Herein is described the first synthesis of SF<sub>5</sub>-ynamides,\nversatile building blocks featuring the pentafluorosulfanyl motif.\nThis synthesis proceeds through a two-step sequence of radical SF<sub>5</sub>-addition onto the π-system of a wide range of terminal\nynamides and derivatives substituted with various nitrogen fragments\nfollowed by a dehydrochlorination reaction. A selection of downstream\nfunctionalization reactions, including nucleophilic additions, cycloadditions,\nand sulfur ylide synthesis, highlights the wide-ranging applications\nof this novel type of functionalized SF<sub>5</sub>-building block.

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Fluorine in Organic Chemistry
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