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DOI: 10.1055/s-0029-1219809
Efficient Iron-Catalyzed Tsuji-Trost Coupling Reaction of Aromatic Allylic Amides through a sp³-Carbon-Nitrogen Breaking
Publication History
Publication Date:
07 April 2010 (online)
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Abstract
The catalytic activation of sp³-carbon-nitrogen of allylic amides is generally difficult because of the inefficient leaving-group ability of the amide group. In this article, we have discovered for the first time that FeCl3-catalyzed Tsuji-Trost coupling reaction of aromatic allylic amides with active methylene compounds, cyclohexanone, and allytrimethylsilane work efficiently under mild conditions.
Key words
iron catalysis - Lewis acid - Brønsted acid - Tsuji-Trost reaction
- Supporting Information for this article is available online:
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References and Notes
General Procedure
for Tsuji-Trost Coupling Reaction of Allylic Amides with
Activated Methylene Compound or Cyclohexanone
A catalytic
amount of FeCl3 (10 mol%) was added to the mixture
of allylic amide (0.5 mmol) and activated methylene compound or
cyclohexanone (0.75 mmol) in MeNO2 (2 mL). After vigorous
stirring at r.t. for the times showed in the Tables and Schemes,
the reaction mixtures were poured into an extraction funnel containing
brine, diluted with distilled H2O and EtOAc. The aqueous
phase was extracted with EtOAc. The combined organic phases were
dried with Na2SO4, and the solvent was removed
under reduced pressure. The crude product was purified by silica
gel column chromatography to furnish the desired products. All the
products are known compounds and confirmed by GC-MS, NMR, and IR
(see spectra).