Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 14-15, Pages 2683-2688Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200250
Keywords
bromofluoroalkenes; difunctionalization; fluorination; silver; terminal alkynes
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Funding
- National Natural Science Foundation of China [20932002, 21172076]
- National Basic Research Program of China (973 Program) [2011CB808600]
- Ministry of Education of China [20090172110014]
- Guangdong Natural Science Foundation [10351064101000000]
- Fundamental Research Funds for the Central Universities [2010ZP0003]
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The difunctionalization of terminal alkynes was achieved with silver fluoride (AgF) and N-bromosuccinimide (NBS) as halogen sources. The presence of the halide moiety greatly enhances the reactivity of the vinyl fluoride compounds that can probably can be transformed into various products that are difficult or even impossible to obtain via direct fluorination. Meanwhile, the monofluoro <.> alkenes were facilely synthesized via a highly chemo- and regioselective fluorination of electron-deficient C C triple bonds using AgF as fluorinating reagent in good yields.
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