181935-82-0Relevant articles and documents
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 (2015)
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.
