A binaphthyl-based primary amine (R)- was designed for the Diels-Alder reaction of alpha-substituted alpha,beta-unsaturated aldehydes; in the presence of the TfOH salt of (R)-, the Diels-Alder reaction of alpha-substituted alpha,beta-unsaturated aldehydes with cyclopentadiene proceeded to afford the corresponding cycloadducts having one all-carbon quaternary stereocenter in good yield with good to high stereoselectivity.
A new synthetic route to 3,3'-dihalo BINAMs based on the direct halogenation of H8-BINAM and subsequent rearomatization to the binaphthyl core has been developed. The combination of this new procedure and Pd-catalyzed coupling reactions enabled us to synthesize various 3,3'-disubstituted BINAMs in only three steps starting from H8-BINAM.
Meso‐to‐meso bithiophene‐bridged cyclic porphyrin 3‐mer, 4‐mer, and 5‐mer were prepared by one‐pot Suzuki–Miyaura coupling reaction. The UV/Vis absorption spectra of the protonated bithiophene–porphyrin hybrid rings indicate the strong intramolecular electronic interactions between porphyrin and bithiophene units. Furthermore, ZnII complexes (see picture for example: Zn pink, N blue, S orange) were shown to serve as multicharge storage systems.
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