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ortho ‐Allylation of 1‐Arylpyrazoles with Allyl Phenyl Ether via Iron‐Catalyzed CH Bond Activation under Mild Conditions
Author(s) -
Asako Sobi,
Norinder Jakob,
Ilies Laurean,
Yoshikai Naohiko,
Nakamura Eiichi
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400063
Subject(s) - chemistry , catalysis , ligand (biochemistry) , electrophile , medicinal chemistry , reagent , ether , coupling reaction , salt (chemistry) , organic chemistry , biochemistry , receptor
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.