Highly enantioselective rhodium-catalyzed cross-coupling of boronic acids and racemic allyl halides was written by Gonzalez, Jesus;van Dijk, Lucy;Goetzke, F. Wieland;Fletcher, Stephen P.. And the article was included in Nature Protocols in 2019.Reference of 68716-49-4 This article mentions the following:
Although Csp2-Csp2 Suzuki-Miyaura couplings (SMCs) are widely used in small-mol. synthesis, related methods that allow the incorporation of Csp3-hybridized coupling partners, particularly in an asym. manner, are less developed. This protocol describes catalytic asym. SMC reactions that provide access to enantiomerically enriched cyclic allylic products. The method couples racemic allyl halide starting materials with sp2-hybridized boronic acid derivatives and is compatible with heterocyclic coupling partners. These reactions are catalyzed by a rhodium-ligand complex and typically display very high levels of enantioselectivity (>95% enantiomeric excess (ee)). In this protocol, a detailed procedure using a dihydropyridine-derived allyl chloride for the synthesis of (-)-(S)-tert-butyl-3-(4-bromophenyl)-3,6-dihydropyridine-1(2H)-carboxylate, an intermediate in the synthesis of the anticancer drug niraparib is reported. This procedure affords 1.17 g (86% yield) of the coupling product with 96% ee. The initial exptl. setup of the reaction takes 45-50 min, and the reaction is complete within 4-5 h. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Reference of 68716-49-4).
2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 68716-49-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts