The versatile and strategic O-carbamate directed metalation group in the synthesis of aromatic molecules : an update

Jansen-van Vuuren, Ross D. (author), Liu, Susana (author), Miah, M. A. Jalil (author), Cerkovnik, Janez (author), Košmrlj, Janez (author), Snieckus, Victor (author)

The aryl O-carbamate (ArOAm) group is among the strongest of the directed metalation groups (DMGs) in directed ortho metalation (DoM) chemistry, especially in the form Ar-OCONEt$_2$. Since the last comprehensive review of metalation chemistry involving ArOAms (published more than 30 years ago), the field has expanded significantly. For example, it now encompasses new substrates, solvent systems, and metalating agents, while conditions have been developed enabling metalation of ArOAm to be conducted in a green and sustainable manner. The ArOAm group has also proven to be effective in the anionic ortho-Fries (AoF) rearrangement, Directed remote metalation (DreM), iterative DoM sequences, and DoM-halogen dance (HalD) synthetic strategies and has been transformed into a diverse range of functionalities and coupled with various groups through a range of cross-coupling (CC) strategies. Of ultimate value, the ArOAm group has demonstrated utility in the synthesis of a diverse range of bioactive and polycyclic aromatic compounds for various applications.

• Language: English
• Keywords: aryl O-carbamate, metalation, rearrangement, cross coupling, regioselective, directing group, aromatic compounds, hydrocarbons, organic compounds
• Work type: Article
• Typology: 1.02 - Review Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2024
• Number of pages: Str. 7731–7828
• Numbering: Vol. 124, iss. 12
• PID: 20.500.12556/RUL-158986
• UDC: 547.52.057
• ISSN on article: 0009-2665
• DOI: 10.1021/acs.chemrev.3c00923
• COBISS.SI-ID: 198743811
• Publication date in RUL: 26.06.2024

Record is a part of a journal

• Title: Chemical reviews
• Shortened title: Chem. rev.
• Publisher: American Chemical Society
• ISSN: 0009-2665
• COBISS.SI-ID: 5125381

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: aril O-karbamat, metalizacija, preureditev, navzkrižna sklopitev, regioselektivnost, usmerjevalna skupina