期刊
ACS CATALYSIS
卷 8, 期 7, 页码 5947-5951出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01341
关键词
monofluoroalkenes; michael acceptors; hydrofluorination; gold catalysis; fluorine
资金
- National Institute of General Medical Sciences [R35 GM118190]
- NSF [DGE 1752814]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM118190] Funding Source: NIH RePORTER
The gold(I)-catalyzed, stereoselective hydro fluorination of electron-deficient alkynes with triethylamine trihydrogen fluoride (Et3N-3HF) is described. Fluorinated alpha,beta-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 beta-alkyl, beta-fluoro Michael acceptors from alkynes. Additionally, the described work expands access to beta-aryl, beta-fluoro Michael acceptors to the synthesis of beta-fluoro-alpha,beta-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.
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