ISSN:
1434-193X
Keywords:
Palladium
;
Allyl complexes
;
Phenolic nucleophiles
;
Chromene
;
C-C couplings
;
Flavonoids
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses of 2-phenyl-2H-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.
Type of Medium:
Electronic Resource
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