Access to N−CF3 Formamides by Reduction of N−CF3 Carbamoyl Fluorides. (23rd November 2022)

• Record Type: Journal Article
• Authors: Zivkovic, Filip G.; D.‐T. Nielsen, Christian; Schoenebeck, Franziska
• Is Part Of: Angewandte Chemie. Volume 134:Number 52(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-11-23
• Subjects: Fluorine -- N−CF3 Formamide -- Reduction; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202213829
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The departure into unknown chemical space is essential for the discovery of new properties and function. We herein report the first synthetic access to N ‐trifluoromethylated formamides. The method involves the reduction of bench‐stable N CF3 carbamoyl fluorides and is characterized by operational simplicity and mildness, tolerating a broad range of functional groups as well as stereocenters. The newly made N −CF3 formamide motif proved to be highly robust and compatible with diverse chemical transformations, underscoring its potential as building block in complex functional molecules. Abstract : The first synthetic access to N ‐trifluoromethylated formamides is reported. The method involves the reduction of bench‐stable N −CF3 carbamoyl fluorides. In contrast to e.g. N −Me formamides, the newly made N −CF3 formamides do not show rotamers at room temperature. Moreover, they are highly robust and compatible with diverse chemical transformations.