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.
No takes yet. Share an insight, caveat, or question.
Nay et al. (1999) studied this question.
Synapse has enriched 3 closely related papers on similar clinical questions. Consider them for comparative context: