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Palladium(II) and bidentate phosphine‐catalyzed selective synthesis of N ‐aryl‐2‐pyrrolidinones via cyclocarbonylative coupling of 2‐aminophenol and 2‐aminothiophenol
Author(s) -
Longo Luigia,
Mele Giuseppe,
Ciccarella Giuseppe,
Sgobba Vito,
Ali Bassam El,
Vasapollo Giuseppe
Publication year - 2002
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.338
Subject(s) - chemistry , pyrrolidinones , palladium , phosphine , catalysis , regioselectivity , aryl , amination , butane , medicinal chemistry , denticity , polymer chemistry , organic chemistry , alkyl , crystal structure
The inter‐ and intra‐molecular regioselective cyclocarbonylative coupling of 2‐aminophenol ( 1a ) and 2‐aminothiophenol ( 1b ) with various allylhalides was achieved in the presence of a catalytic amount of palladium acetate and 1,4‐bis(diphenylphosphino)butane to afford N ‐aryl‐2‐pyrrolidinones ( 3 , 4 ) in 47–65% yields. Other aminophenol derivatives have also been used and gave good yields of the corresponding N ‐aryl‐2‐pyrrolidinones. Copyright © 2002 John Wiley & Sons, Ltd.