Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis was written by Sarie, Jerome C.;Thiehoff, Christian;Neufeld, Jessica;Daniliuc, Constantin G.;Gilmour, Ryan. And the article was included in Angewandte Chemie, International Edition in 2020.Quality Control of Methyl 3,5-dihydroxy-4-iodobenzoate This article mentions the following:
The chromane nucleus is common to a plenum of bioactive small mols. where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl Ph ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Quality Control of Methyl 3,5-dihydroxy-4-iodobenzoate).
Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Quality Control of Methyl 3,5-dihydroxy-4-iodobenzoate
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com