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Volumn 6, Issue 3, 2004, Pages 433-436

Heck-Type Arylation of 2-Cycloalken-1-ones with Arylpalladium Intermediates Formed by Decarboxylative Palladation and by Aryl Iodide Insertion

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYL GROUP; CYCLOALKENE; IODINE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE;

EID: 1342327964     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0363467     Document Type: Article
Times cited : (226)

References (34)
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    • German Patent DE 3827675, Aug 16, 1988
    • Heck-type coupling reactions of aryl halides with 2-cycloalken-1-ones have been reported in the patent literature, without mention of coupling efficiency. We have not obtained more than 30% yield in the coupling of 4-bromobenzonitrile with 2-cyclohexen-1-one by the method reported in the following patent reference (two attempts): Sucrow, W.; Fiedel, D.; Poetsch, E.; Rädecker, G. German Patent DE 3827675, Aug 16, 1988.
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    • note
    • 4; the dried solution was filtered, and the filtrate was concentrated. Purification of the residue by flash column chromatography afforded the 3-aryl-2-cycloalken-1-one product, typically in 50-90% yield.
  • 31
    • 1342274798 scopus 로고    scopus 로고
    • note
    • Structure 3 is believed to be the (E)-stereoisomer, as shown. This assignment is based upon one-dimensional NOESY experiments.


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