NDLI: Radical Arylation of Phenols, Phenyl Ethers, and Furans

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Radical Arylation of Phenols, Phenyl Ethers, and Furans

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kolb, Roman Heinrich, Markus R. Pratsch, Gerald Wetzel, Alexander
Description	Author Affiliation: Wetzel A ( Department für Chemie und Biochemie, Organische Chemie 1, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.)
Abstract	Radical arylations of para-substituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titanium(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access to diversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxy groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a β-secretase inhibitor and the synthesis of a calcium-channel modulator.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	8
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-02-22
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Furans Chemistry Phenols Phenyl Ethers Amyloid Precursor Protein Secretases Antagonists & Inhibitors Chemical Synthesis Calcium Channel Blockers Catalysis Diazonium Compounds Free Radicals Hydrochloric Acid Molecular Structure Solvents Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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