Copper-catalyzed crosscoupling of vinyl nitrenes and CF₃-carbenes to synthesize CF₃-2-azadienes

Abstract

A unique and efficient copper catalytic system has been established for the synthesis of fluorinated 2-azadienes from isoxazoles and CF3-N-tosylhydrazones via crosscoupling reactions of vinyl nitrenes with fluoroalkyl carbenes.

Expedient Synthesis of gem-CF2-2H-Thiophenes from Enaminothiones

“…Thus, it would be appealing for wide audiences from interdisciplinary science to design a powerful yet reliable strategy to construct 2H-thiophenes containing fluorine atoms in the core rings. In our continuing interests in enaminone and carbene chemistry, [20][21][22][23][24][25][26] we envisioned that the possibilities of preparing fluorinated S-heterocycles by cyclization of enaminothiones with fluorinated carbenes, which are both easily available starting materials. Herein, we present an efficient avenue for the synthesis of fluorinated 2H-thiophenes via a formal [4+1] cyclization of enaminothiones and fluorinated carbene precursors under very mild reaction conditions without any metal catalysts (Figure 1).…”

Nickel-Catalyzed Multicomponent Assembly of Alkynes toward α-CF3-Alkenes

“…Despite the widespread application of fluoroalkyl hydrazones in two-component reactions as unique donor-fluorinated carbene precursors for synthesizing various fluorine-containing molecules by the groups of Wang, Bi, Jiang, and others, their utilization in multicomponent reactions has been surprisingly underexplored. Meanwhile, alkynes and boron reagents, which are pivotal motifs in organic synthesis, have also been investigated for their reactivity with diazo compounds to generate trisubstituted alkenes through 1,1-difunctional terminal alkynes in MCRs .…”