Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

Abstract

Copper catalysis and, more generally, copper chemistry are pivotal for modern organofluorine chemistry. Major advances have been made in the field of trifluoromethylselenolations of organic compounds where copper catalysis played a crucial role. Recent developments in this field are highlighted in this minireview.

Insights into the Recent Synthetic Advances of Organoselenium Compounds

“…The transformations include direct selenylations, selenocyclizations, selenoxide eliminations and 2,3-sigmatropic rearrangements. [34] Researchers have successfully reviewed staggering progress being made in the direction of organoselenium compounds focussing on their catalytic efficiency in various significant reactions, [34][35][36][37][38] greener prospects [39] and therapeutic significance of different class of organoselenium compounds. [16,40] This review focuses on the recent progress made in the organoselenium chemistry in last 3 years which has not been covered in earlier reviewed content entailing the advances made in the field.…”

“…The transformations include direct selenylations, selenocyclizations, selenoxide eliminations and 2,3‐sigmatropic rearrangements [34] . Researchers have successfully reviewed staggering progress being made in the direction of organoselenium compounds focussing on their catalytic efficiency in various significant reactions, [34–38] greener prospects [39] and therapeutic significance of different class of organoselenium compounds [16,40] …”

Stable and Storable N(CF3)2 Transfer Reagents

“…Because of their easy accessibility using silver(I) fluoride and the respective perfluoroalkene, for example, heptafluoropropene and tetrafluoroethylene, [15] they are of increasing interest. Similarly, copper(I) and silver(I) complexes with perfluorinated ligands that are coordinated via oxygen, sulfur, or selenium to the coinage metal have recently come into focus and have been established as transfer reagents for perfluorinated groups, for example for trifluoromethoxylation, [19–20] trifluoromethylthiolation, [21–22] and trifluoromethylselenolation reactions [23–24] . So far, only few Cu I and Ag I metal complexes with the trifluoromethoxy ligand like [(Ph t Bu 2 P)(bpy)AgOCF 3 ] [25] are known (Figure 1).…”

“…Similarly, copper(I) and silver(I) complexes with perfluorinated ligands that are coordinated via oxygen, sulfur, or selenium to the coinage metal have recently come into focus and have been established as transfer reagents for perfluorinated groups, for example for trifluoromethoxylation,[ 19 , 20 ] trifluoromethylthiolation,[ 21 , 22 ] and trifluoromethylselenolation reactions. [ 23 , 24 ] So far, only few Cu I and Ag I metal complexes with the trifluoromethoxy ligand like [(Ph t Bu 2 P)(bpy)AgOCF 3 ] [25] are known (Figure 1 ). [ 25 , 26 , 27 ] The small number of structurally characterized complexes is due to the low stability of the OCF 3 – ion that easily loses F – while releasing carbonyl fluoride (difluorophosgene), which enabled the use of AgOCF 3 as C(O)F 2 source.…”

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…Thus, nowadays, copper catalysis has attracted enormous attention from synthetic organic chemists. Several review articles collected and described the recent progress made in pleasing and exceptional copper catalysis in all areas of synthetic transformations (Monnier and Taillefer, 2013 ; Guo et al, 2015 ; Thapa et al, 2015 ; Tandon, 2019 ; Ghiazza and Tlili, 2020 ). Copper-based catalysts are also extensively employed in different chemical industries (Punniyamurthy and Rout, 2008 ).…”