Iron-catalyzed selective oxidative arylation of phenols and biphenols

Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling

“…8 The Pappo group has showcased use of iron-catalyzed, consecutive oxidative cross-couplings to prepare phlorotannin natural products. 9 In oxidative coupling of phenols, control of chemo-, regio-, and stereoselectivity are significant challenges. Such issues have been recently studied in a number of different contexts.…”

Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes

“…Our research commenced by applying oxidative phenol–phenol coupling conditions [FeCl 3 (10 mol %), t -BuOO t -Bu (1.5 equiv), HFIP, and room temperature], which were developed by our group, 1a , 4 , 5b , 14 for reacting 2-naphthol 1a (1.5 equiv) with 2-aminonaphthalene 2a (1 equiv). Fortunately, this reaction proceeded smoothly, affording ( rac )-NOBIN 3 in 82% yield ( Figure 2 ).…”

“…Iron-catalyzed oxidative phenol coupling reactions 1 bring together phenols with unfunctionalized C–H nucleophiles such as 1,3-dicarbonyl compounds, 2 conjugated alkenes, 3 arenes, polyaromatic hydrocarbons (PAHs), 2b , 4 and a second phenolic coupling partner. 5 This method is considered to be highly attractive in terms of step- and atom-economy for assembling new phenolic architectures.…”

Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C−C and C−O Coupling

“…Undoubtedly, such oxidation events occur in an umber of other reported dimerizations. [10][11][12][13][14][15][16][17] In most cases,t he oxidation would be readily reversible,allowing the dimer to accumulate.Inother cases,such oxidation gives rise to decomposition. Ahallmark of this reaction is the ability of the oxidized dimer to engage in selective C À Ob ond formation with an additional monomer.…”