Facile synthesis of carbamoyl fluorides via N-carbamoylimidazole activation

Meden, Anže (author), Knez, Damijan (author), Gobec, Stanislav (author)

The untapped potential of carbamoyl fluorides for various chemico/biological applications is hampered by the scarcity of straightforward and benign methods for their synthesis. In this report, we disclose a novel mild three-step procedure that avoids exotic, corrosive, and highly toxic reagents. Briefly, commercially available secondary amines are carbamoylated with 1,1′-carbonyldiimidazole, followed by alkylation to improve nucleofugality, and exchange with inorganic KF. This procedure works on a gram scale without chromatographic purification. It is however limited to basic, sterically unhindered secondary amines without alkylation-prone functional groups.

• Language: English
• Keywords: anions, column chromatography, nuclear magnetic resonance spectroscopy, silica, solvents
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2025
• Number of pages: Str. 6908–6917
• Numbering: Vol. 10, iss. 7
• PID: 20.500.12556/RUL-167623
• UDC: 543.057
• ISSN on article: 2470-1343
• DOI: 10.1021/acsomega.4c09438
• COBISS.SI-ID: 226589187
• Publication date in RUL: 04.03.2025

Record is a part of a journal

• Title: ACS omega
• Shortened title: ACS omega
• Publisher: American Chemical Society
• ISSN: 2470-1343
• COBISS.SI-ID: 525873945

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: sinteza karbamoil fluoridov, aktivacija N-karbamoilimidazola

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0208
• Name: Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin

• Funder: ARIS - Slovenian Research and Innovation Agency
• Funding programme: Young researchers