Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 8, Pages 2547-2556Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902927
Keywords
diazonium salts; biaryls; phenols; phenyl ethers; radical reactions
Categories
Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft (DFG)
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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 obtamed from hydroxy- and alkoxy-substituted benzylamines, phenethyl-amines, 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 beta-secretase inhibitor and the synthesis of a calcium-channel modulator.
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