103517-22-2Relevant articles and documents
Steric Effects in the 17O NMR Spectroscopy of Aromatic Methyl Ethers
Wysocki, M. A.,Jardon, P. W.,Mains, G. J.,Eisenbraun, E. J.,Boykin, D. W.
, p. 331 - 334 (1987)
17O NMR spectroscopic data (natural abundance) were obtained for 19 methoxy-aromatic compounds: a series of substituted anisoles with a single ortho substituent, a series of 2,6-disubstituted anisoles, a series of 3-substituted-1,2-dimethoxybenzenes and t
Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1 H-Benzotriazoles with Arylboronic Acids
Singh, Manish K.,Lakshman, Mahesh K.
, p. 4156 - 4162 (2016/01/09)
1-(Aryl)methoxy-1H-benzotriazoles (ArCH2OBt) are bench-stable reagents that are prepared readily from 1H-benzotriazol-1-yl-4-methylbenzenesulfonate and benzylic alcohols. These compounds, which contain a N-O-C bond, undergo cross-coupling with arylboronic acids by C-O bond scission with catalysts that comprise Pd(OAc)2 and biarylphosphine ligands. Such reactivity of ArCH2OBt derivatives, which lead to diarylmethanes, has not been described previously and constitutes a new activation of benzylic alcohols. With regard to the various ligand-metal complexes that support catalytic activity, it appears that those with smaller "percent buried volumes" (%Vbur) provide better outcomes. This factor has been evaluated in the initial optimization studies and in further reactions with difficult coupling partners. Ligand electronics of the biaryl moiety seem to play a lesser role in this type of reaction. The biscoordinating bis[(2-diphenylphosphino)phenyl] ether appears to be suitable to improve the yields of low-yielding reactions. Phosphine fine: 1-(Aryl)methoxy-1H-benzotriazoles (ArCH2OBt), which contain a N-O-C bond, undergo cross-coupling with arylboronic acids by C-O bond scission with catalysts that comprise Pd(OAc)2 and biarylphosphine ligands. Such reactivity of ArCH2OBt derivatives, which lead to diarylmethanes, has not been described previously and constitutes a new activation of benzylic alcohols.
