1578-33-2Relevant articles and documents
Synthesis of the spirocyclic core of the prunolides using a singlet oxygen-mediated cascade sequence
Sofikiti, Nikoletta,Tofi, Maria,Montagnon, Tamsyn,Vassilikogiannakis, Georgios,Stratakis, Manolis
, p. 2357 - 2359 (2005)
(Chemical Equation Presented) A highly efficient and rapid four-step synthesis of the bis-spiroketal core of the prunolide natural products, starting from furan itself, is described. The key step and culmination of the synthesis, responsible for zipping up the spirocyclic core, is a singlet oxygen-orchestrated cascade sequence in which a double photooxygenation of a 1,2-difuryl alkene precursor precedes dehydration and spirocyclization to furnish the intact prunolide core.
Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers
Lik, Artur,Fritze, Lars,Müller, Lars,Helten, Holger
supporting information, p. 5692 - 5695 (2017/05/04)
Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to the synthesis of arylborane molecules 4a-c, oligomers 8a,b, and polymers 8a′,b′. Photophysical investigations, supported by TD-DFT calculations, reveal highly effective π-conjugation in thienyl- and furylborane species; the latter are also highly emissive.
CO2 Conversion into Esters by Fluoride-Mediated Carboxylation of Organosilanes and Halide Derivatives
Frogneux, Xavier,Von Wolff, Niklas,Thuéry, Pierre,Lefèvre, Guillaume,Cantat, Thibault
supporting information, p. 2930 - 2934 (2016/03/25)
A one-step conversion of CO2 into heteroaromatic esters is presented under metal-free conditions. Using fluoride anions as promoters for the C-Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO2 in the C-Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO2 into a polyester material for the first time. Metal free! A novel methodology is described to convert CO2 into heteroaromatic esters in the presence of organosilanes and organic halides using fluoride anions as promoters for the C-Si bond activation (see scheme). CO2 exhibits a unique catalytic influence in the C-Si bond cleavage of pyridylsilanes, serving as a traceless activator.
