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- Title
Triethylamine‐Mediated Transformation of Phosphonates into Phosphonamidates.
- Authors
Backx, Simon; Dejaegere, Andreas; Simoens, Andreas; Van de Poel, Jef; Krasowska, Dorota; Stevens, Christian V.; Mangelinckx, Sven
- Abstract
Organophosphorus compounds such as phosphonamidates are gaining attention across different fields of chemistry, with interesting applications as pharmaceuticals, or pesticides. However, practical application of phosphonamidates is complicated by their difficult syntheses which often involve expensive or unstraightforward reagents and harsh conditions. To remedy these issues, we present a flexible, room temperature synthesis for novel P‐alkylphosphonamidates without the need for intermediary purification. Commonly available phosphonates are first chlorinated by use of oxalyl chloride and phosphonylaminium salts are used to mediate the harsh reactivity of phosphonochloridates, giving rise to the desired products. We demonstrate the compatibility of our protocol with primary and secondary amines, as well as with different phosphonate esters. The proposed pathway also enables the synthesis of primary phosphonamidates using ammonium acetate as a cheap and safe alternative for ammonia. In future research, this protocol will also enable the synthesis of bioactive targets that are incompatible with current protocols.
- Subjects
OXALYL chloride; AMMONIUM acetate; SECONDARY amines; ESTERS; SALTS; PHOSPHONATES; ORGANOPHOSPHORUS compounds
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 26, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300172