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An Easy One‐Pot Synthesis of Diverse 2,5‐Di(2‐pyridyl)pyrroles: A Versatile Entry Point to Metal Complexes of Functionalised, Meridial and Tridentate 2,5‐Di(2‐pyridyl)pyrrolato Ligands
Author(s) -
McSkimming Alex,
Diachenko Vera,
London Rachel,
Olrich Kiara,
Onie C. Jessica,
Bhadbhade Mohan M.,
Bucknall Martin P.,
Read Roger W.,
Colbran Stephen B.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402157
Subject(s) - chemistry , disproportionation , ligand (biochemistry) , pyrrole , substituent , metal , ketone , electrocatalyst , electrochemistry , medicinal chemistry , bipyridine , combinatorial chemistry , polymer chemistry , catalysis , organic chemistry , crystal structure , electrode , biochemistry , receptor
A wide variety of 2,5‐di(2‐pyridyl)pyrroles (dppHs) substituted at the C3 and C4 positions of the pyrrole core were obtained by direct condensation of a 2‐pyridylcarboxaldehyde (2 equiv), an α‐methylene ketone with at least one electron‐withdrawing substituent and ammonium acetate. A novel 2,5‐di(1,10‐phenanthrolin‐2‐yl)pyrrole was also characterised. The dppHs provide a direct, quick entry to dipyridylpyrrolato (dpp − )–metal complexes. The meridial tridentate dpp − ligand is a useful anionic analogue of the terpyridyl ligand. The first (dpp)Ru complexes are described; the 3,4‐substitution of the central pyrrole significantly perturbs the potentials of the redox processes of these complexes. A [(dpp)Ru(bpy)(MeCN)] + (bpy=2,2′‐bipyridine) complex is an electrocatalyst for the reductive disproportionation of carbon dioxide to carbon monoxide and the carbonate ion.