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Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling
Author(s) -
Huang Lin,
Gu Yiting,
Fürstner Alois
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900865
Subject(s) - ring (chemistry) , catalysis , 2 pyridone , coupling (piping) , chemistry , coupling reaction , medicinal chemistry , combinatorial chemistry , materials science , organic chemistry , metallurgy
In the presence of simple iron salts, 2‐pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6‐addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non‐thermodynamic Z,E ‐configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.