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Neutral Lipophilic Palladium(II) Complexes and their Applications in Electrocatalytic Hydrogen Production and C‐C Coupling Reactions
Author(s) -
CuzanMunteanu Olesea,
Sirbu Dumitru,
Giorgi Michel,
Shova Sergiu,
Gibson Elizabeth A.,
Réglier Marius,
Orio Maylis,
Martins Luísa M. D. R. S.,
Benniston Andrew C.
Publication year - 2020
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201901283
Subject(s) - chemistry , palladium , benzotriazole , catalysis , inorganic chemistry , electrochemistry , trifluoroacetic acid , electrode , organic chemistry
Three neutral palladium(II) complexes [Pd(L n ) 2 ] ( n = 1,2,3) containing benzotriazole‐phenolate ligands HL 1 = 2‐(2H‐benzotriazol‐2‐yl)‐6‐dodecyl‐4‐methylphenol; HL 2 = 2‐(2H‐benzotriazol‐2‐yl)‐4,6‐di‐tert‐pentylphenol; HL 3 = 2‐(2H‐benzotriazol‐2‐yl)‐4,6‐bis(1‐methyl‐1‐phenylethyl)phenol were synthesized and characterized by several spectroscopic methods ( 1 H, 13 C NMR, UV‐Visible), ESI mass spectrometry and single‐crystal X‐ray diffraction. The geometry around the palladium(II) centre for each complex is described as distorted square planar. The complexes were tested as potential catalysts for electrochemical proton reduction in DMF using trifluoroacetic acid (TFA). Gas analysis under electrocatalytic conditions at a boron‐doped diamond working electrode confirmed the hydrogen production. After performing similar gas analysis experiments using a working mercury pool electrode, no hydrogen was detected which supports the concept that the active species of the catalytic process are palladium particles formed on the surface of the working electrode. The palladium(II) benzotriazolyl phenolate complexes facilitate the formation of particles for electrocatalytic hydrogen production. Furthermore, the palladium(II) complexes PdL 2 and PdL 3 were able to catalyse microwave‐assisted Heck and Sonogashira C–C coupling reactions.