A bis(amino)cyclopropenylidene-catalyzed direct method for the synthesis of α,α'-diarylated ketones from aromatic as well as heteroaromatic aldehydes has been developed. This unprecedented organocatalytic protocol offers access to a wide range of α,α'-diarylated ketones in moderate to excellent yields under mild conditions through umpolung of aldehydes followed by 1,6-conjugate addition with para-quinone methides.
A highly chemoselective
intermolecular crossed acyloin condensation
between aromatic aldehydes and trifluoroacetaldehyde ethyl hemiacetal
has been developed under mild reaction conditions using N-heterocyclic carbene as a catalyst. A wide range of aromatic aldehydes
bearing electron-withdrawing and -donating substituents underwent
a smooth transformation to their corresponding trifluoromethyl containing
acyloin derivatives in moderate to good yields.
A mild and efficient method for the synthesis of unsymmetrical diaryl- and triarylmethanes through a B(CF) catalyzed reduction of para-quinone methides and fuchsones respectively, using the Hantzsch ester as a reducing source has been developed. Detailed mechanistic investigations revealed that the reaction actually proceeds through a Lewis acid-base pair complex derived from B(CF) and the Hantzsch ester.
A competent method for the synthesis of indolizine‐based diarylmethylphosphonates is described. This protocol involves a metal‐catalyzed 5‐endo‐dig‐cyclization of 2‐(2‐enynyl)pyridine derivatives followed by a remote addition of diarylphosphites to provide indolizine‐containing diarylmethylphosphonates in good yields.
An efficient protocol for the synthesis of unsymmetrical allyl diarylmethanes through a Lewis acid catalysed 1,6-conjugate addition of allylsilanes to para-quinone methides is described.
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