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Palladium‐Catalyzed Rapid Methoxylation and Deuteriomethoxylation of Bromo–chalcones: Uncovering the Catalytic Activity of the Pd/ t BuXPhos Catalyst System
Author(s) -
Rangarajan T. M.,
Singh Rishi Pal,
Singh R. P.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601761
Subject(s) - catalysis , chemistry , nucleophile , palladium , ligand (biochemistry) , reductive elimination , medicinal chemistry , alkyl , combinatorial chemistry , organic chemistry , receptor , biochemistry
We report an unprecedented t BuXPhos ligand ( L3 ) supported Pd‐catalyzed rapid methoxylation and deuteriomethoxylation of bromo‐chalcones (5 to 40 min.) with excellent yields. Pd/RockPhos ( L2 ) catalytic system also facilitates the coupling reaction, but the reaction time is fairly longer than Pd/ t BuXPhos ( L3 ) catalytic system. The coupling of MeOH/MeOH‐ d 4 with 4‐bromo‐chalcones is so rapid than that of 3‐bromo‐chalcones, which clearly indicates that the former proceeds through a pure electronic pathway of reductive elimination. These catalyst systems facilitate the coupling of 4‐bromo‐chalcones even with higher alkyl alcohols relatively long reaction time that implies the efficiency and rate of coupling relays on the nucleophilicity of the alcohols. This methodology may be adopted for the 11 C‐radiolabeling of organic compounds for PET imaging applications.