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Phenols as C ‐ and O ‐Nucleophiles in Palladium‐Catalysed Allylic Substitutions
Author(s) -
Nay Bastien,
Peyrat JeanFrançois,
Vercauteren Joseph
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k
Subject(s) - chemistry , nucleophile , phenols , cinnamyl alcohol , palladium , allylic rearrangement , phloroglucinol , organic chemistry , cinnamaldehyde , aryl , medicinal chemistry , hemiacetal , catalysis , alkyl
Syntheses of 2‐phenyl‐2 H ‐chromene (3‐flavene) and cinnamaldehyde aryloxy‐hemiacetal, involving nucleophilic substitution by phenols of the π‐allyl palladium complex formed from the acylal of cinnamaldehyde in the presence of catalytic amounts of palladium(0) (10 mol‐%), are presented. Alternatively, the corresponding alcohol acetates furnish 1,3‐diarylpropenes and cinnamyl aryl ethers. Our results demonstrate the potent C ‐nucleophilicity of phloroglucinol in Tsuji–Trost reactions in flavonoid synthesis, and again illustrate the already well established O ‐nucleophilicity of phenols.