New and efficient dehalogenative coupling and reduction of α-haloketones with active nickel complex. Facile syntheses of 1,4-diketones and bicyclo[4.2.O]oct-3-ene-2,5-diones
✍ Scribed by Masahiko Iyoda; Masahiro Sakaitani; Atsuko Kojima; Masaji Oda
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 233 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The active nickel complex generated in situ by reduction of NiBr2(PPh3)2 with zinc in the presence of Et4NI is a useful reagent for the dehalogenative coupling of phenacyl halides to 1,4-diaryl-1,4-diketones and for the dechlorination of 3,4-dichlorobicyclo[4.2.0]octane-2,5-diones to bicyclo[4.2.0]oct-3-ene-2,5-diones. Although several zerovalent nickel complexes exhibit specific ability in a reductive coupling of aryl or alkenyl halides,l) little is known about the nickel-catalyzed coupling of a-haloketones or reductive dehalogenation of vie-dihalides.*) Recently, we have reported