This review aims to provide a comprehensive overview of condensation-based methods for the C–H bond functionalization of amines that feature azomethine ylides as key intermediates. These transformations are typically redox-neutral and share common attributes with classic name reactions such as the Strecker, Mannich, Friedel−Crafts, Pictet−Spengler, and Kabachnik−Fields reaction, while incorporating a redox-isomerization step. This approach provides an ideal platform to rapidly transform simple starting materials into complex amines.
Palladium(II)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohol to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceed via...
A remarkable base-promoted methodology for rapid construction of the (E)- and (Z)-γ-oxo-α,β-alkenoic esters skeleton involved with readily accessed vinyl propargylic alcohols through modified redox isomerization was uncovered. This approach manifested...
New water-soluble, N-heterocyclic carbene (NHC) or mixed NHC/tertiary phosphine complexes [RhCl(cod)(sSIMes)], Na2[Rh(bmim)(cod)(mtppts)], and [Rh(bmim)(cod)(pta)]BF4 were synthetized and applied for the first time as catalysts in redox isomerization of allylic alcohols in aqueous media. [RhCl(cod)(sSIMes)] (with added sulfonated triphenylphosphine) and [Rh(bmim)(cod)(pta)]BF4 catalyzed selectively the transformation of allylic alcohols to the corresponding ketones. The highest catalytic activity, TOF = 152 h−1 (TOF = (mol reacted substrate) × (mol catalyst × time)−1) was observed in redox isomerization of hept-1-en-3-ol ([S]/[cat] = 100). The catalysts were reused in the aqueous phase at least three times, with only modest loss of the catalytic activity and selectivity.
Borane Catalyzed Redox Isomerization of 2‐Amino Chalcones: Hydride Abstraction or Hydride Migration?
