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Diarylmethanes through an Unprecedented Palladium‐Catalyzed C−C Cross‐Coupling of 1‐(Aryl)methoxy‐1 H ‐Benzotriazoles with Arylboronic Acids
Author(s) -
Singh Manish K.,
Lakshman Mahesh K.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500818
Subject(s) - chemistry , moiety , aryl , catalysis , reactivity (psychology) , palladium , ligand (biochemistry) , reagent , bond cleavage , coupling reaction , ether , medicinal chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , medicine , biochemistry , alkyl , alternative medicine , receptor , pathology
1‐(Aryl)methoxy‐1 H ‐benzotriazoles (ArCH 2 OBt) are bench‐stable reagents that are prepared readily from 1 H ‐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 ArCH 2 OBt 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” (% V bur ) 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.