Radical Arylation of Phenols, Phenyl Ethers, and Furans

• Autor: Wetzel, Alexander ; Pratsch, Gerald ; Kolb, Roman ; Heinrich, Markus R.
• Assuntos: Amino acids ; Amyloid Precursor Protein Secretases - antagonists & inhibitors ; Amyloid Precursor Protein Secretases - chemical synthesis ; Amyloid Precursor Protein Secretases - chemistry ; biaryls ; Calcium Channel Blockers - chemical synthesis ; Calcium Channel Blockers - chemistry ; Catalysis ; Chemistry ; Chlorides ; Diazonium Compounds - chemical synthesis ; Diazonium Compounds - chemistry ; diazonium salts ; Ethers ; Free Radicals - chemistry ; Furans ; Furans - chemical synthesis ; Furans - chemistry ; Hydrochloric Acid - chemistry ; Molecular Structure ; Phenols ; Phenols - chemical synthesis ; Phenols - chemistry ; phenyl ethers ; Phenyl Ethers - chemical synthesis ; Phenyl Ethers - chemistry ; Phenyls ; radical reactions ; Radicals ; Solvents ; Solvents - chemistry ; Stereoisomerism
• É parte de: Chemistry : a European journal, 2010-02, Vol.16 (8), p.2547-2556
• Notas: ArticleID:CHEM200902927
  ark:/67375/WNG-6KZT8Q0B-P
  Deutsche Forschungsgemeinschaft
  DFG
  Fonds der Chemischen Industrie
  istex:0EAF65D59AD0A322F920FEF56DBF5BA84FC2EA67
  ObjectType-Article-1
  SourceType-Scholarly Journals-1
  ObjectType-Feature-2
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• Descrição: 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. A revelation in arylation! Radical arylations of para‐substituted phenols, phenyl ethers, and furans proceed with good regioselectivity at the ortho position of hydroxy‐ or alkoxy‐substituted phenyls or at the 2‐position of furans. The reactions are conducted with arenediazonium salts as aryl radical sources, titanium(III) chloride as the reductant, and diluted hydrochloric acid as the solvent (see scheme).
  
• Editor: Weinheim: WILEY-VCH Verlag
  
• Idioma: Inglês