Iron pentacarbonyl mediated coupling of benzyl halides to ketones under mild phase transfer conditions.
✍ Scribed by Guy Tanguy; Bernd Weinberger; Herve´ des Abbayes
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 190 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
In a two-phase system (saturated aqueous caLGum hydroxide, tetrab-utyZanunonium sulfate, dichZoromethane, iron pentacarbonyl) benzy2 bromides are readily carbonylated to dibenzyZ ketones ; c1-~1' dibromoortkoxylene yields the o-q&no&methane iron tricarbony2 complex 8. It 7:s inferred that the reactions proceed through transient generation of the tetracarbony2 Serrate dianion.
There is now increasing interest in synthetic applications of metal carbonyls I under phase transfer conditions . We recently showed that, under such conditions, iron pentacarbonyl is a valuable catalyst for the carbonylation of benzyl halides 1 to arylacetic acids 3 2 -.
-Here we wish to report that under a nitrogen atmosphere, and using a mildly basic aqueous medium, this system conveniently gives the symmetrical ketones 2 (reaction 1).