Phenols as C- and O-nucleophiles in palladium-catalysed allylic substitutions

Bastien Nay; Jean François Peyrat; Joseph Vercauteren

doi:10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k

Phenols as C- and O-nucleophiles in palladium-catalysed allylic substitutions

Bastien Nay, Jean François Peyrat, Joseph Vercauteren

Univ. Bordeaux

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2231-2234
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	9
DOIs	https://doi.org/10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k
Publication status	Published - 1 Jan 1999
Externally published	Yes

Keywords

Allyl complexes
C-C couplings
Chromene
Flavonoids
Palladium
Phenolic nucleophiles

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10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k

Cite this

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title = "Phenols as C- and O-nucleophiles in palladium-catalysed allylic substitutions",

abstract = "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.",

keywords = "Allyl complexes, C-C couplings, Chromene, Flavonoids, Palladium, Phenolic nucleophiles",

author = "Bastien Nay and Peyrat, \{Jean Fran{\c c}ois\} and Joseph Vercauteren",

year = "1999",

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doi = "10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k",

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journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - Phenols as C- and O-nucleophiles in palladium-catalysed allylic substitutions

AU - Nay, Bastien

AU - Peyrat, Jean François

AU - Vercauteren, Joseph

PY - 1999/1/1

Y1 - 1999/1/1

N2 - 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.

AB - 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.

KW - Allyl complexes

KW - C-C couplings

KW - Chromene

KW - Flavonoids

KW - Palladium

KW - Phenolic nucleophiles

U2 - 10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k

DO - 10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k

M3 - Article

AN - SCOPUS:0032865560

SN - 1434-193X

SP - 2231

EP - 2234

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Phenols as C- and O-nucleophiles in palladium-catalysed allylic substitutions

Abstract

Keywords

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