Synthesis and application of a new fluorous-tagged ammonia equivalent

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Simon Dalsgaard Nielsen, Garrick Smith, Mikael Begtrup, Jesper Langgaard Kristensen

A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluorous N--O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.
Original languageEnglish
JournalChemistry: A European Journal
Volume16
Issue number15
Pages (from-to)4557-4566
ISSN0947-6539
DOIs
Publication statusPublished - 2010

Bibliographical note

Keywords: ammonia equivalents; cleavage reactions; flourous synthesis; itopride; molybdenum

ID: 19345237