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Donor‐Acceptor Substituted 2‐Phenylpyridines by Means of Reductive C,C–C ross Coupling Reaction
Author(s) -
Triller Sebastian,
Dittmann Tim,
Bendig Mareike,
Schnelle Jan,
Friedmann Tom,
Heck Jürgen
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600707
Subject(s) - catalysis , chemistry , acceptor , pyridine , substrate (aquarium) , reductive elimination , coupling reaction , nickel , combinatorial chemistry , coupling (piping) , medicinal chemistry , organic chemistry , materials science , physics , oceanography , geology , metallurgy , condensed matter physics
The preparation of 2‐phenylpyridines decorated with an electron donating and accepting unit, which are potentially suitable to induce second harmonic generation, was performed by means of reductive nickel catalyzed C,C ‐cross coupling reaction, developed by Gosmini et. al. We were successful to obtain the desired 2‐phenylpyridines directly from donor‐functionalized arylhalides and acceptor‐modified 2‐halopyridines with a cheap and easy to prepare Ni catalyst. It turned out that even the presence of hydroxy groups and carboxylic acids are tolerated in this reaction, whereas in the case of a formyl group containing pyridine substrate no C,C ‐coupled product was obtained. However, the coupling was successful when the formyl function was protected by an acetal formation.