Flipping the Metalation of 4‐Dimethylaminopyridine: Steric Repulsion versus London Dispersion Attraction

URN to cite this document:: urn:nbn:de:bvb:355-epub-597295
DOI to cite this document:: 10.5283/epub.59729

Verkhov, Valery A. ; Gubanova, Alexandra N. ; Tonkoglazova, Daria I. ; Tupikina, Elena Yu.

; Antonov, Alexander S.

License: Creative Commons Attribution Non-commercial No Derivatives 4.0
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Date of publication of this fulltext: 03 Dec 2024 09:45

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Abstract

Non-covalent interactions, including the coordination of an organolithium reagent by a directing group and the steric hindrance from substituents, play a crucial role in determining the selectivity of metalation reactions. Here, we demonstrate the effective utilization of steric interactions for flipping the lithiation of 4-dimethylaminopyridine (DMAP). Introduction of a Me3Si substituent to the ...