Progress in metal-catalysed trifluormethylation reactions using hypervalent iodine reagents

Abstract

The trifluoromethyl group is found in a variety of pharmaceuticals, agrochemicals, and functional organic compounds due to its ability to improve properties like electronegativity, hydrophobicity, metabolic stability, binding selectivity, and bioavailability. As a result, the development of innovative techniques for the incorporation of trifluoromethyl group has long been a research focus. Various metals such as Cu, Mg, Ni, Ag, Fe, and V were found to act as lewis acid in the synthesis of different trifluoromethylated compounds. In this review, the recent development of metal-catalyzed trifluoromethylation of C-C, C-N, C-O multiple/single bonds using hypervalent iodine reagent is described.

Organohypervalent heterocycles

“…Benziodoxoles containing a trifluoromethyl group (-CF 3 group) as a ligand are known as Togni's reagents. [571][572][573][574] Trifluoromethylbenziodoxoles can be conveniently prepared from the corresponding acetoxy-or methoxybenziodoxoles by the addition of TMSCF 3 . These compounds are excellent reagents for the selective transfer of the -CF 3 group to various substrates under metal-free, transition metal-catalyzed, or photocatalyzed conditions.…”

Recent Progress in Synthetic Applications of Cyclic Hypervalent Iodine(III) Reagents

“…Benziodoxoles with trifluoromethyl group as a ligand are known as Togni's reagents. [79][80][81][82] Trifluoromethylbenziodoxoles are useful reagents for a highly selective transfer of trifluoromethyl group to various substrates under metal-free, transition metal-catalyzed, or photocatalyzed conditions. Trifluoromethyl group is particularly important in pharmaceuticals and therefore these reagents have important synthetic applications.…”

“…Reactions of trifluoromethylbenziodoxoles with alkenes or alkynes can lead to the addition of trifluoromethyl groups, as well as trifluoromethyl group addition followed by cyclization. [80][81][82]100] The other reactions involve the insertion of trifluoromethyl groups into C(sp 3 )À H and C(sp 2 )À H bonds and trifluoromethylation at heteroatoms. The following text describes recent examples of such reactions.…”

“…Benziodoxoles with trifluoromethyl group as a ligand are known as Togni's reagents [79–82] . Trifluoromethylbenziodoxoles are useful reagents for a highly selective transfer of trifluoromethyl group to various substrates under metal‐free, transition metal‐catalyzed, or photocatalyzed conditions.…”

“…Numerous examples of reactions of trifluoromethylbenziodoxoles with various organic substrates have been reported. Reactions of trifluoromethylbenziodoxoles with alkenes or alkynes can lead to the addition of trifluoromethyl groups, as well as trifluoromethyl group addition followed by cyclization [80–82,100] . The other reactions involve the insertion of trifluoromethyl groups into C( sp 3 )−H and C( sp 2 )−H bonds and trifluoromethylation at heteroatoms.…”