67024-46-8Relevant articles and documents
N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading
Berkessel, Albrecht,Biswas, Animesh,Harnying, Wacharee,Sudkaow, Panyapon
supporting information, p. 19631 - 19636 (2021/08/09)
We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.
Rhenium complex as a useful catalyst for acylative cleavage of ethers
Umeda, Rui,Kaiba, Kenta,Tanaka, Toshimasa,Takahashi, Yuuki,Nishimura, Takashi,Nishiyama, Yutaka
experimental part, p. 3089 - 3091 (2011/02/25)
It was found that a rhenium complex such as ReBr(CO)5 acts as an efficient catalyst for the acylative cleavage of the carbon-oxygen bond of ethers with acyl chloride, giving the corresponding esters in moderate to good yields.
2-Acyloxy-4,6-dimethoxy-1,3,5-triazine - A new reagent for ester synthesis
Kaminska, Janina E.,Kaminski, Zbigniew J.,Gora, Jozef
, p. 593 - 596 (2007/10/03)
2-Acyloxy-4,6-dimethoxy-1,3,5-triazines obtained in reaction between carboxylic acid and 2-chloro-4,6-dimethoxy-1,3,5-triazine were used as acylating agents for the synthesis of esters from primary, secondary, and tertiary alcohols. Because of mild acylation conditions the method could be applied to esterification of labile alcohols with aromatic and aliphatic (also α-branched) acids in good yields.