Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides was written by Levin, Mark D.;Ovian, John M.;Read, Jacquelyne A.;Sigman, Matthew S.;Jacobsen, Eric N.. And the article was included in Journal of the American Chemical Society in 2020.COA of Formula: C8H7IO4 This article mentions the following:
An iodoarene-catalyzed (R,R)/(S,S)I (R = Ph, 3-chlorophenyl, 3,4,5-trifluorophenyl, 2-Me Ph, etc.; R1 = Me, Bn) enantioselective synthesis of β,β-difluoroalkyl bromide (R)-R2C(F2)CH(Br)R3 (R2 = 3-nitropenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 1-methyl-1H-pyrazol-4-yl, etc.; R3 = Me, Et, nBu, iPr, etc.) building blocks was reported. The transformation involves an oxidative rearrangement of α-bromostyrenes R2C(Br)=CHR3, utilizing HF-pyridine as the fluoride source and m-CPBA as the stoichiometric oxidant. A catalyst decomposition pathway was identified, which, in tandem with catalyst structure-activity relationship studies, facilitated the development of an improved catalyst providing higher enantioselectivity with lower catalyst loadings. The versatility of the difluoroalkyl bromide products was demonstrated via highly enantiospecific substitution reactions with suitably reactive nucleophiles. The origins of enantioselectivity were investigated using computed interaction energies of simplified catalyst and substrate structures, providing evidence for both CH-π and π-π transition state interactions as critical features. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7COA of Formula: C8H7IO4).
Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.COA of Formula: C8H7IO4
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com