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4,4″‐Disubstituted Terpyridines and Their Homoleptic Fe II Complexes
Author(s) -
Harzmann Gero D.,
Neuburger Markus,
Mayor Marcel
Publication year - 2013
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.201300231
Subject(s) - homoleptic , chemistry , terpyridine , steric effects , suzuki reaction , boronic acid , crystal structure , coupling reaction , yield (engineering) , crystallography , stereochemistry , combinatorial chemistry , organic chemistry , palladium , catalysis , metal , materials science , metallurgy
A novel synthetic route to 4,4″‐disubstituted‐2,2′:6′,2″‐terpyridine ligands by Suzuki–Miyaura cross‐coupling was elaborated by synthesizing compounds 4a – 5c . The considerable stability of 4‐substituted lithium triisopropyl 2‐pyridylborates 2a – c , which are less prone to protodeboronation than similarly functionalized neutral boronic acid derivatives, enabled this synthetic route. The terpyridine core structure was further functionalized by exposing 4,4″‐dichloroterpyridine ( 4b ) to Suzuki coupling conditions to yield 4,4″‐diarylterpyridines 5a – c . Homoleptic Fe II complexes 8a – f of the reported terpyridine ligands were formed quantitatively, which demonstrates the lack of steric repulsion of substituents at the 4‐ and 4″‐positions during complexation. The solid‐state structures of particular ligands and Fe II complexes were analyzed by single‐crystal X‐ray crystallography. UV/Vis absorption data for the Fe II complexes are also provided to complement the results reported here.