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Pacman and Hangman Metal Tetraazamacrocycles
Author(s) -
Lee Chang Hoon,
Villágran Dino,
Cook Timothy R.,
Peters Jonas C.,
Nocera Daniel G.
Publication year - 2013
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201300068
Subject(s) - palladium , chemistry , catalysis , acetonitrile , metal , polymer chemistry , organic chemistry
Metal complexes of derivatized 2,12‐dimethyl‐3,7,11,17‐tetraazabicyclo[11.3.1]heptadeca‐1(17),2,11,13,15‐pentane (bapa) ligands were prepared from 4‐substituted diacetylpyridine derivatives by templated condensation with 3,3′‐diaminodipropylamine in the presence of a metal halide or nitrate. The diacetylpyridine derivatives with Pacman and Hangman scaffolds are delivered from borylation of the 4‐postion of diacetylpyridine and subsequent Suzuki coupling with the appropriate Hangman or Pacman backbone. Electrochemical examination of the parent [Co(bapa)] 2+ scaffold reveals it to be a catalyst for the hydrogen evolution reaction (HER) in acetonitrile. Similar studies of the Hangman complex appear to be obscured by trace amounts of residual palladium remaining from the Suzuki coupling reaction to provide a cautionary note for the use of such cross‐coupling methodologies in the preparation of HER catalysts.