Oxidative Halogenation of Arenes, Olefins and Alkynes Mediated by Iodine(III) Reagents

Abstract

: Iodine(III)-based reagents has been broadly used in oxidative reactions for the structural functionalization with several functional groups. Among the more relevant and useful synthetic transformations using these hypervalent γ 3 -reagents, it can be found the fluorination, chlorination, bromination as well as the iodination protocols. Herein, we present some of the most representatives oxidative halogenation procedures of arenes, olefins and alkynes dating from the oldest to the more recent advances in the area, highlighting the discovery and application of new iodine(III)-based halogenating species.

Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds

“…[4] Concerning this research, nitrogen-containing compounds, specifically those with the indole core, are among the most important group of heterocycles which are present in hundreds of pharmacological active drugs and treatments. [5][6][7][8][9][10][11] Synthetic methods for accessing to this class of active compounds involves in general, the use of metal free [12][13][14][15][16][17][18][19][20][21][22][23][24] or metal catalyzed [25,26] strategies. In the context of this work, we referred to indomethacin, as an indole-containing drug, considered one of the most efficient anti-inflammatories which acts as nonselective COX-1 and COX-2 inhibitor.…”

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

“…Iodine(III) chemistry has had an explosive development over the last twenty years [1–3] as an efficient and green oxidative alternative to the traditional protocols [4–6] that involves toxic transition metals or strong reaction conditions. Concerning the aromatic substitution, the introduction of different groups in these systems, overall requires, the $${{_{{\rm sp}{^{3}}}}}$$ C−H functionalization [7] .…”

Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine

“…Conversions of alkenes to vicinal diols, 1 aminoalcohols, 2 and diamines 3 are prized transformations for their utility in chemical synthesis, with applications ranging from small molecules to complex natural products. 4,5 By analogy, alkene haloesterification reactions are pathways to these functional groups in two steps, and offer divergent pathways that leverage the carbon–halogen bond's intermediacy to sulfur-, phosphorous-, nitrogen-, and oxygen–carbon bond formation, in addition to reduction. Broad interest in alkene haloesterification reactions was reignited with the advent of enantioselective variants, 6 but the intramolecular cyclizations are restricted to small ring-sizes that form β-, γ-, and δ-lactones.…”