79186-29-1Relevant articles and documents
Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Reactions of Aldehyde Acyl Anions with either Diarylmethyl or Allylic Carbonates
Yasuda, Shigeo,Ishii, Takuya,Takemoto, Shunsuke,Haruki, Hiroki,Ohmiya, Hirohisa
, p. 2938 - 2942 (2018)
Benzylation and allylation of aldehyde acyl anions were enabled by the merger of a thiazolium N-heterocyclic carbene (NHC) catalyst and a palladium/bisphosphine catalyst in a synergistic manner. Owing to the mildness of the reaction conditions, various functional groups were tolerated in the substrates.
Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes
Garapati, Venkata Krishna Rao,Gravel, Michel
supporting information, p. 6372 - 6375 (2018/10/15)
Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.
Chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reactions: Importance of the fused ring in triazolium salts
Langdon, Steven M.,Wilde, Myron M.D.,Thai, Karen,Gravel, Michel
supporting information, p. 7539 - 7542 (2014/06/10)
Morpholinone- and piperidinone-derived triazolium salts are shown to catalyze highly chemoselective cross-benzoin reactions between aliphatic and aromatic aldehydes. The reaction scope includes ortho-, meta-, and para-substituted benzaldehyde derivatives with a range of electron-donating and -withdrawing groups as well as branched and unbranched aliphatic aldehydes. Catalytic loadings as low as 5 mol % give excellent yields in these reactions (up to 99%).
