Unusual Ligand Directed Regioselectivity in the Iron Catalyzed Cross Coupling of Allylic Ethers to 2‐Substituted 1,3‐Dienes

James M. Takacs, Lawrence G. Anderson, G. V.Bindu Madhavan, Franklin L. Seely

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

C4 of 1 is always preferentially attacked in (L)Fe0‐catalyzed reactions with 2. Whether the product of 1,2 addition, 3, or that of 1,4 addition, 4, predominates depends strongly on L, as does the relative proportion of the products formed by attack on C1; e.g., for R  CH2Ph and L  2,2′‐bipyridine, 3:4 = 73:27 (89% of the total yield); for R  CH2Ph and L  2,2′‐biquinoline, 3:4 = 6:94 (64%). R  CH2Ph, CH2C6H11, tetrahydropyranyl. (Figure Presented.)

Original languageEnglish (US)
Pages (from-to)1013-1015
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume26
Issue number10
DOIs
StatePublished - Oct 1987
Externally publishedYes

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Regioselectivity
Ethers
Iron
Ligands

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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Unusual Ligand Directed Regioselectivity in the Iron Catalyzed Cross Coupling of Allylic Ethers to 2‐Substituted 1,3‐Dienes. / Takacs, James M.; Anderson, Lawrence G.; Madhavan, G. V.Bindu; Seely, Franklin L.

In: Angewandte Chemie International Edition in English, Vol. 26, No. 10, 10.1987, p. 1013-1015.

Research output: Contribution to journalArticle

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abstract = "C4 of 1 is always preferentially attacked in (L)Fe0‐catalyzed reactions with 2. Whether the product of 1,2 addition, 3, or that of 1,4 addition, 4, predominates depends strongly on L, as does the relative proportion of the products formed by attack on C1; e.g., for R  CH2Ph and L  2,2′‐bipyridine, 3:4 = 73:27 (89{\%} of the total yield); for R  CH2Ph and L  2,2′‐biquinoline, 3:4 = 6:94 (64{\%}). R  CH2Ph, CH2C6H11, tetrahydropyranyl. (Figure Presented.)",
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AB - C4 of 1 is always preferentially attacked in (L)Fe0‐catalyzed reactions with 2. Whether the product of 1,2 addition, 3, or that of 1,4 addition, 4, predominates depends strongly on L, as does the relative proportion of the products formed by attack on C1; e.g., for R  CH2Ph and L  2,2′‐bipyridine, 3:4 = 73:27 (89% of the total yield); for R  CH2Ph and L  2,2′‐biquinoline, 3:4 = 6:94 (64%). R  CH2Ph, CH2C6H11, tetrahydropyranyl. (Figure Presented.)

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