Dual Role of (NH₄)₂CO₃ Enables Defluorinative Synthesis of β-Fluoroalkylated Aminovinyl Ketones

Abstract

A modular multicomponent reaction of readily available fluoroalkyl alkenes, amidines, ammonium carbonate, and water was developed for the facile construction of β-fluoroalkylated aminovinyl ketones, which provided chemists a novel access to value-added organofluorine compounds. The reaction proceeded regio-/stereoselectively under mild conditions and exhibited good functional group tolerance. Cheap, stable, and low-toxic inorganic salt (NH 4 ) 2 CO 3 was first found to act as both a nitrogen source and a carbonyl equivalent in the multi-bond-forming process.

Photoinduced copper-catalyzed C–N coupling with trifluoromethylated arenes

“…Consequently, carbazole-centered PNP ligand ( L1 ) was introduced to achieve copper-catalyzed C–N coupling of trifluoromethylated arenes and anilines. To our surprise, the resulting α,α-difluoromethylamines was immediately transformed to imidoyl fluorides through tandem C–N coupling and defluorination under basic conditions (Supplementary Table 10 ) 66 . Despite of the promising synthetic potential of imidoyl fluorides, their synthesis is challenging and in general harsh reaction conditions are required while with limited scope 67 – 70 .…”

Direct Fluoroacylation of Indole with Perfluoroalkyl Iodides

“…Based on the above and previous results, ,,,− we proposed a possible mechanism as shown in Scheme . Initially, in the presence of Na 2 S 2 O 4 , perfluoroalkanesulfinate (C 4 F 9 SO 2 Na, A ) was generated from C 4 F 9 I. , Then the perfluoroalkylated compound ( B ) was produced by coupling of C 4 F 9 SO 2 Na and indoles .…”