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Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of ?-Fluoro Michael Acceptors.

ABSTRACT: The gold(I)-catalyzed, stereoselective hydrofluorination of electron-deficient alkynes with triethylamine trihydrogen fluoride (Et3N·3HF) is described. Fluorinated ?,?-unsaturated aldehydes, amides, esters, ketones, and nitriles were isolated in moderate to good yields as single diastereomers. In all but four cases, the (Z)-vinyl fluorides were initially formed in ?97% diastereoselectivity. This work constitutes the first catalytic example of the diastereoselective preparation of a variety of ?-alkyl, ?-fluoro Michael acceptors from alkynes. Additionally, the described work expands access to ?-aryl, ?-fluoro Michael acceptors to the synthesis of ?-fluoro-?,?-unsaturated amides and nitriles. The monofluoroalkenes formed through this strategy were readily transformed into other fluorine-containing compounds, and the developed method was applied to the synthesis of a fluorinated analogue of Exoderil, a topical antimycotic.

SUBMITTER: O'Connor TJ 

PROVIDER: S-EPMC6874379 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of <i>β</i>-Fluoro Michael Acceptors.

O'Connor Thomas J TJ   Toste F Dean FD  

ACS catalysis 20180604 7

The gold(I)-catalyzed, stereoselective hydrofluorination of electron-deficient alkynes with triethylamine trihydrogen fluoride (Et<sub>3</sub>N·3HF) is described. Fluorinated <i>α,β</i>-unsaturated aldehydes, amides, esters, ketones, and nitriles were isolated in moderate to good yields as single diastereomers. In all but four cases, the (<i>Z</i>)-vinyl fluorides were initially formed in ≥97% diastereoselectivity. This work constitutes the first catalytic example of the diastereoselective prepa  ...[more]

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