4.3 Article

Heck reaction with 3-fluoro-3-buten-2-one

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 129, Issue 10, Pages 983-985

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2008.02.006

Keywords

Heck reaction; Fluorovinyl ketone; Palladium coupling; Fluorobenzalacetone

Funding

  1. National Science Foundation

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3-Fluoro-3-buten-2-one (2) is readily prepared from 1-fluoro-l-chloro-2-methoxy-2-methylcyclopropane (1) in 82% yield by heating the cyclopropane in aqueous quinoline solution. Ketone 2 reacts with aryl iodides (3) in a Heck reaction catalyzed by Pd(OAc)(2) to give Z-3-fluorobenzalacetones (4) in 36-86% yield. (C) 2008 Elsevier B.V. All rights reserved.

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