Palladium-catalyzed ortho alkoxylation of oxazoline derivatives: An avenue to reach meta-substituted electron-rich arenes via employing a traceless directing group

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.

《钯催化邻位烷氧基化（palladium-catalyzed ortho alkoxylation）恶唑啉衍生物（oxazoline derivatives）：通过无痕导向基团（traceless directing group）合成间位取代富电子芳烃的新途径》一文的分析数据与化合物编号（论文编号 vs. 电子实验记录本（ELN）条目）

该论文于2024年10月25日发表于《ACS Omega》
DOI: 10.1021/acsomega.4c04389
作者：拉赫勒·普尔卡维赫、丹尼斯·斯瓦特内克、迈克尔·施努尔希

资助单位：奥地利科学基金（FWF，项目编号P33064-N）

背景与方法
本文报道了一种高效且区域选择性优异的钯催化邻位烷氧基化反应。该反应在空气氛围和温和温度（60°C）下进行。一系列醇可作为烷氧基化试剂并同时充当反应溶剂，其中伯醇和仲醇均适用。此外，氟化醇也可应用，以引入药学相关的含氟基团。1,3-二烷氧基化产物可进一步水解，将恶唑啉导向基团转化为羧酸；若需要，羧酸可通过脱羧反应去除。该方法能够逆转亲电芳香取代反应（electrophilic aromatic substitution reactions）的传统位点选择性，因为它可合成具有1,3-位二给电子基团的芳烃。

本出版物及其支持信息可在出版商网站上以开放获取文件形式获取（参见上述DOI）。已上传手稿支持信息中所有化合物的详细分析原始数据文件。此外，还上传了名为File code for compounds.pdf的PDF文件，该文件应能清晰地将论文中给出的化合物编号与ELN中的相应条目及相应分析数据文件关联起来。

技术细节
上传的文件包含由内部布鲁克光谱仪记录的核磁共振（NMR）谱的自由感应衰减信号（FIDs）。需要使用NMR谱显示软件，如MestreNova或Topspin。
高分辨质谱（HRMS）数据也已上传，需通过MassHunter软件处理。