14 research outputs found
Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes
Alkyltriflones in the RambergBacklund Reaction: An Efficient and Modular Synthesis of gem-Difluoroalkenes
Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Tertiary Sulfones
We
describe the development of a nickel-catalyzed Suzuki–Miyaura
cross-coupling of tertiary benzylic and allylic sulfones with arylboroxines.
A variety of tertiary sulfones, which can easily be prepared via a
deprotonation–alkylation route, were reacted to afford symmetric
and unsymmetric quaternary products in good yields. We highlight the
use of either BrettPhos or Doyle’s phosphines as effective
ligands for these challenging desulfonative coupling reactions. The
utility of this methodology was demonstrated in the concise synthesis
of a vitamin D receptor modulator analogue
Enantiospecific Cross-coupling of Cyclic Alkyl Sulfones
Methods to form carbon-carbon bonds efficiently and with control of stereochemistry are critical for the construction of complex molecules. Cross-coupling reactions are among the most efficient and widely used reactions to construct molecules, with reactions enabling the retention or installation of chirality as recent additions to this powerful toolbox. Sulfones are robust, accessible organic electrophiles that have many attractive features as cross-coupling partners, however since the first example of their use in 1979, there have been no examples of their use in enantio-selective, -specific or -convergent cross-couplings. The high acidity of sulfones makes it unclear whether this transformation is even possible outside tertiary systems. Herein we report the enantiospecific cross-coupling of cyclic sulfones and Grignard reagents. Up to 99% chirality transfer is observed despite the strong basicity of the Grignard components. In situ monitoring reveals that the cross-coupling is kinetically competitive with competing deprotonation, resulting in a highly enantioselective transformation
Water-Soluble N-Heterocyclic Carbene-Protected Gold Nanoparticles: Size-Controlled Synthesis, Stability, and Optical Properties
Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
A scandium-triflate-catalyzed
arylative desulfonation of diarylmethyl
phenyl sulfones with arenes and heteroarenes was established. A variety
of both sulfone and arene substrates were reacted to afford symmetric
and nonsymmetric triarylmethanes in good yields. Further transformations
of the resulting triarylmethanes and application to the concise synthesis
of a bactericidal agent analogue were also demonstrated