Abstract
A practical and mild strategy has been developed for the cross-coupling
of O-arylation of phenol with differently substituted aryl halides
and heteroaryl iodides using low catalyst loading of copper iodide
under low operating temperature in DMF with TMHD as the ligand and
Cs2 CO3 as the base. This method tolerates a
variety of functional groups including sterically hindered phenols and
heteroaryl iodides to afford products in good to excellent yields (up
to 95%).
Key words
cross-coupling - mild conditions - low catalyst
loading - copper-catalyzed - O-arylations - phenol
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8 Representative Procedure for O-Arylation
of Phenols: A mixture of CuI (Sigma-Aldrich, 99.99% purity,
0.0147 mmol), TMHD (0.147 mmol), Cs2 CO3 (2.94
mmol) was dissolved in DMF (0.3 mL). Subsequently, the aryl halide (1.47
mmol) and the phenol (2.21 mmol) were added to the reaction vial
and a screw cap was fitted to it. The reaction mixture was stirred
under air in a closed system at 60 ˚C for 24 h and the
heterogeneous mixture was then cooled to r.t. and diluted with EtOAc.
The resulting solution was directly filtered through a pad of Celite.
The organic extracts were washed with H2 O twice. The
combined organic extracts were dried with anhyd Na2 SO4 and
the solvent was removed under reduced pressure. The crude product
was purified by silica gel column chromatography to afford the O-arylated product.
The identity and purity of known products were confirmed by ¹ H
NMR and ¹³ C NMR spectroscopic analysis.
