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Arylation of N ‐Methyl‐2‐oxindole with Arylboronic Acids in Water Catalyzed by Palladium(II) Pincer Complexes with a Low Catalyst Loading
Author(s) -
Vignesh Arumugam,
Kaminsky Werner,
Dharmaraj Nallasamy
Publication year - 2017
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.201601411
Subject(s) - catalysis , chemistry , oxindole , palladium , yield (engineering) , pincer movement , aqueous solution , aryl , organic chemistry , aqueous medium , homogeneous , materials science , alkyl , physics , metallurgy , thermodynamics
Two new Pd II ONO pincer complexes were utilized efficiently as homogeneous catalysts for the site‐selective C3‐arylation of N ‐methyl‐2‐oxindole with arylboronic acids at room temperature in aqueous media to yield a series of 3‐aryl‐ N ‐methyl‐2‐oxindoles. This catalytic reaction progressed well with a low catalyst loading (0.01 mol %) under open‐flask conditions. Notably, a column‐chromatography‐free method for the quantitative preparation of C3‐arylated N ‐methyl‐2‐oxindoles is reported. The catalyst showed good compatibility with wide range of substrates with recyclability in up to five consecutive runs without an appreciable loss of yield.