Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions

Sobi Asako, Jakob Norinder, Laurean Ilies, Naohiko Yoshikai, Eiichi Nakamura

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C-H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.

Original languageEnglish
Pages (from-to)1481-1485
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number7
DOIs
Publication statusPublished - May 5 2014
Externally publishedYes

Fingerprint

Allylation
Ethers
Iron
Chemical activation
Ligands
Ether
Salts
phenyl allyl ether

Keywords

  • allylation
  • arenes
  • C-H activation
  • iron
  • pyrazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions. / Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 7, 05.05.2014, p. 1481-1485.

Research output: Contribution to journalArticle

Asako, Sobi ; Norinder, Jakob ; Ilies, Laurean ; Yoshikai, Naohiko ; Nakamura, Eiichi. / Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions. In: Advanced Synthesis and Catalysis. 2014 ; Vol. 356, No. 7. pp. 1481-1485.
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