Effective synthesis of aryl ethers and coumaranones employing the palladium-catalyzed enyne-diyne [4 + 2] cycloaddition protocol

Vladimir Gevorgyan, Long Guo Quan, Yoshinori Yamamoto

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Alkyl-, alkoxy-, and aryloxy-substituted conjugated enynes 1 in the presence of Pd(PPh3)4 catalyst smoothly underwent the regiospecific [4 + 2] cycloaddition reaction with conjugated alkyl- and alkoxy-substituted symmetric diynes 2 to give multisubstituted aryl ethers 3 in good to high yields. Benzannulation of enynes 1d-g with unsymmetric diyne 6, possessing alkyl and alkoxy groups at acetylenic terminii, in most cases produced an aromatic product 8 with an alkoxy group of diyne attached to the ethynyl moiety of the aromatic product. Remarkably, alkoxy-substituted diynes 2c and 6 underwent the benzannulation reaction with 1 at an unusually low temperature of 0 °C! One-pot consecutive benzannulation of alkyl-substituted enynes 1d,e and alkoxy-substituted enynes 1f,g with alkoxy-substituted diynes 2c and 6 followed by protonolysis with TsOH afforded coumaranones 9a-c and 10 in reasonable to high overall yields.

Original languageEnglish (US)
Pages (from-to)568-572
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number2
DOIs
StatePublished - Jan 28 2000
Externally publishedYes

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Ethers
Cycloaddition
Palladium
Diynes
alkoxyl radical
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Effective synthesis of aryl ethers and coumaranones employing the palladium-catalyzed enyne-diyne [4 + 2] cycloaddition protocol. / Gevorgyan, Vladimir; Quan, Long Guo; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 65, No. 2, 28.01.2000, p. 568-572.

Research output: Contribution to journalArticle

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N2 - Alkyl-, alkoxy-, and aryloxy-substituted conjugated enynes 1 in the presence of Pd(PPh3)4 catalyst smoothly underwent the regiospecific [4 + 2] cycloaddition reaction with conjugated alkyl- and alkoxy-substituted symmetric diynes 2 to give multisubstituted aryl ethers 3 in good to high yields. Benzannulation of enynes 1d-g with unsymmetric diyne 6, possessing alkyl and alkoxy groups at acetylenic terminii, in most cases produced an aromatic product 8 with an alkoxy group of diyne attached to the ethynyl moiety of the aromatic product. Remarkably, alkoxy-substituted diynes 2c and 6 underwent the benzannulation reaction with 1 at an unusually low temperature of 0 °C! One-pot consecutive benzannulation of alkyl-substituted enynes 1d,e and alkoxy-substituted enynes 1f,g with alkoxy-substituted diynes 2c and 6 followed by protonolysis with TsOH afforded coumaranones 9a-c and 10 in reasonable to high overall yields.

AB - Alkyl-, alkoxy-, and aryloxy-substituted conjugated enynes 1 in the presence of Pd(PPh3)4 catalyst smoothly underwent the regiospecific [4 + 2] cycloaddition reaction with conjugated alkyl- and alkoxy-substituted symmetric diynes 2 to give multisubstituted aryl ethers 3 in good to high yields. Benzannulation of enynes 1d-g with unsymmetric diyne 6, possessing alkyl and alkoxy groups at acetylenic terminii, in most cases produced an aromatic product 8 with an alkoxy group of diyne attached to the ethynyl moiety of the aromatic product. Remarkably, alkoxy-substituted diynes 2c and 6 underwent the benzannulation reaction with 1 at an unusually low temperature of 0 °C! One-pot consecutive benzannulation of alkyl-substituted enynes 1d,e and alkoxy-substituted enynes 1f,g with alkoxy-substituted diynes 2c and 6 followed by protonolysis with TsOH afforded coumaranones 9a-c and 10 in reasonable to high overall yields.

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