Oxy-difluoroallylation\nof Ynamides by Nickel-Catalyzed\nTandem Alkoxylation/Claisen Rearrangement

A nickel-catalyzed tandem alkoxylation/claisen\nrearrangement\nstrategy\nfor the oxy-difluoroallylation of ynamides has been developed. In\nthis reaction, 3,3-difluoroallyl alcohol was used as a fluorine-containing\nbuilding block to construct the C–CF<sub>2</sub> bond for the\nfirst time. This approach is recognized for its robust tolerance of\nfunctional groups, impressive yields, and excellent atomic efficiency,\nall achieved under mild reaction conditions. A series of β,β-difluoromethyleneamide\nderivatives were efficiently obtained through simple operations, and\ntheir practicality was confirmed through gram-scale synthesis and\nproduct derivatization.

Publication Details

Journal
Figshare
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.orglett.4c03232.s001
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Oxy-difluoroallylation\nof Ynamides by Nickel-Catalyzed\nTandem Alkoxylation/Claisen Rearrangement

Figshare
Catalytic Alkyne Reactions
article

Oxy-difluoroallylation\nof Ynamides by Nickel-Catalyzed\nTandem Alkoxylation/Claisen Rearrangement

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Abstract

A nickel-catalyzed tandem alkoxylation/claisen\nrearrangement\nstrategy\nfor the oxy-difluoroallylation of ynamides has been developed. In\nthis reaction, 3,3-difluoroallyl alcohol was used as a fluorine-containing\nbuilding block to construct the C–CF<sub>2</sub> bond for the\nfirst time. This approach is recognized for its robust tolerance of\nfunctional groups, impressive yields, and excellent atomic efficiency,\nall achieved under mild reaction conditions. A series of β,β-difluoromethyleneamide\nderivatives were efficiently obtained through simple operations, and\ntheir practicality was confirmed through gram-scale synthesis and\nproduct derivatization.

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Openalex Percentile: Top 72%
Catalytic Alkyne Reactions
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Oxy-difluoroallylation\nof Ynamides by Nickel-Catalyzed\nTandem Alkoxylation/Claisen Rearrangement · Figshare (2024) | TGRS Research Map | TGRS