Metal-Free Markovnikov-Type Alkyne Hydration under Mild Conditions
2016; American Chemical Society; Volume: 18; Issue: 9 Linguagem: Inglês
10.1021/acs.orglett.6b00801
ISSN1523-7060
AutoresWenbo Liu, Haining Wang, Chao‐Jun Li,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoA Markovnikov-type alkyne hydration protocol is presented using 20% CF3SO3H (TfOH) as the catalyst under unprecedented mild conditions applicable to various alkynes, including terminal arylalkynes, terminal nonfunctionalized aliphatic alkynes, and internal alkynes with excellent regioselectivity in good to excellent yields (average yields >85%). The reaction procedure operates under mild conditions (25-70 °C), with broad functional group compatibility, and uses only slightly more than a stoichiometric amount of water in the absence of any transition metal. The success of this protocol hinges upon the utilization of trifluoroethanol as the solvent.
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