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Zinc‐Catalyzed Stereo‐ and Regioselective 1,4‐Hydrative Fluorination of 3‐En‐1‐ynamides with Selectfluor
Author(s) -
Jadhav Appaso Mahadev,
Huple Deepak B.,
Singh Rahulkumar Rajmani,
Liu Rai Shung
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201501021
Subject(s) - selectfluor , chemistry , regioselectivity , zinc , catalysis , acetonitrile , electrophile , stereoselectivity , medicinal chemistry , organic chemistry , combinatorial chemistry
Zinc‐catalyzed 1,4‐oxofluorinations of 3‐en‐1‐ynamides with Selectfluor in acetonitrile/water proceeded with high regio‐ and stereoselectivity, giving E ‐configured γ‐fluoro‐α,β‐unsaturated amides efficiently. Our control experiments indicate that kinetically unstable C‐bound zinc dienolates are chemically reactive to undergo S E 2′‐electrophilic fluorinations whereas the detectable O‐bound dienolates preferably undergo protodemetalation reactions instead.