98954-44-0Relevant academic research and scientific papers
Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
Trost, Barry M.,Kalnmals, Christopher A.
supporting information, p. 9066 - 9074 (2018/06/29)
A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
Efficient catalytic, oxidative lactonization for the synthesis of benzodioxepinones using thiazolium-derived carbene catalysts
Rose, Christopher A.,Zeitler, Kirsten
supporting information; experimental part, p. 4552 - 4555 (2010/12/25)
An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions. The react
Synthesis of calix[4]crowns containing soft donor atoms and a study of their metal-cation binding properties: Highly selective receptors for Cu2+
Ashram, Muhammad
, p. 1662 - 1668 (2007/10/03)
Two new calix[4]arenethiacrown derivatives 1 and 2 in the cone conformation were synthesized by two different pathways in good yield. Their complexation properties toward alkali, alkaline earth and transition metal cations were studied in acetonitrile at 298.15 K using a conductometric titration technique. The selectivity for Cu2+ over other cations with these novel ligands was excellent.
