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- Title
ortho-Allylation of 1-Arylpyrazoles with Allyl Phenyl Ether via Iron-Catalyzed CH Bond Activation under Mild Conditions.
- Authors
Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi
- 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 CH activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.
- Subjects
PYRAZOLES; PHENYL ethers; IRON; CARBON-hydrogen bonds; ALLYLATION
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 7, p1481
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201400063