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An acetatopalladium(II) complex with 1‐benzyl‐ N ‐(3,5‐di‐ tert ‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides
Author(s) -
Keesara Srinivas,
Narendra Babu G.,
Pal Samudranil
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3778
Subject(s) - chemistry , pincer movement , catalysis , amine gas treating , halide , proton nmr , schiff base , medicinal chemistry , base (topology) , metal , stereochemistry , organic chemistry , mathematical analysis , mathematics
The Schiff base 1‐benzyl‐ N ‐(3,5‐di‐ tert ‐butylsalicylidene)piperidin‐4‐amine (HL) and its acetatopalladium(II) complex having the formula [Pd(L)(OAc)] were synthesized. Both HL and [Pd(L)(OAc)] were characterized using elemental analysis and various spectroscopic (infrared, UV–visible, 1 H NMR and 13 C NMR) and mass spectrometric measurements. The molecular structure of the complex was determined using X‐ray crystallographic analysis. In the complex, the pincer‐like NNO‐donor L − and the monodenate OAc − provide a distorted square‐planar N 2 O 2 coordination environment around the metal centre. The physicochemical properties and the spectroscopic features of [Pd(L)(OAc)] are consistent with its molecular structure. The complex was found to be an effective catalyst for the Suzuki–Miyaura cross‐coupling reactions of hydroxyaryl halides with arylboronic acids in predominantly aqueous media. The reactions afforded hydroxybiaryl products in good to excellent yields with a wide substrate scope.