Analytical Data and Compound Numbering (in paper numbering vs. ELN entries) for the Publication entitled:"Palladium-catalyzed ortho alkoxylation of oxazoline derivatives: An avenue to reach meta-substituted electron-rich arenes via employing a traceless directing group"

The paper was published on 2024-10-25 in ACS Omega

DOI: 10.1021/acsomega.4c04389

Authors: Raheleh Pourkaveh, Dennis Svatunek, Michael Schnürch

Funded by the Austrian Science Fund (FWF, project number P33064-N) 

Context and methodology

An efficient and highly regioselective palladium-catalyzed oxazoline-directed alkoxylation is reported. The reaction proceeds under air and mild temperatures (60 °C). A series of alcohols can be used as alkoxylating agents and concomitantly act as reaction solvents, whereas primary and secondary alcohols are tolerated. Furthermore, fluorinated alcohols can be applied as well, introducing pharmaceutically relevant fluorine-containing groups. 1,3-Dialkoxylated products can be further subjected to hydrolysis transforming the oxazoline-directing group to a carboxylic acid, which can be removed by decarboxylation if desired. This approach demonstrates the capability to reverse the conventional site selectivity of electrophilic aromatic substitution reactions, since it allows the synthesis of arenes with two electron-donating groups in a 1,3-relationship.

The publication and its Supporting Information can be found as open-access files on the publisher's website (see DOI above).

All detailed files containing the analytical raw data, for all compounds given in the Supporting Information of the manuscript are uploaded. An additional pdf file named File code for compounds.pdf is uploaded, that should clearly link the compound number given in the paper to the respective entry in the ELN and the respective analytical data files. 

Technical details

The files uploaded contain the FIDs of NMR spectra recorded by an in-house Bruker Spectrometer. A software to display NMR-spectra is needed, such as MestreNova or Topspin).

HRMS data is uploaded too and has to be processed via MassHunter software.