119-52-8Relevant articles and documents
Reduction of 1,2-diketones with titanium tetraiodide: A simple approach to α-hydroxy ketones
Hayakawa,Sahara,Shimizu
, p. 7939 - 7942 (2000)
1,2-Diketones are readily reduced with titanium tetraiodide to give α-hydroxy ketones in good to excellent yields. Regioselectivity on the reduction of unsymmetrical substrates is also discussed. (C) 2000 Elsevier Science Ltd.
N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins
Haghighi, Ali Javaheri,Mokhtari, Javad,Karimian, Khashayar
, p. 1646 - 1652 (2021)
N-PEGylated-thiazolium salt is used as efficient catalyst for the benzoin condensation. The catalyst was synthesized by reaction of activated polyethylene glycol 10,000 (PEG-10000) with 4-methyl-5-thiazoleethanol (sulfurol). Reaction mixture undergoes temperature-assisted phase transition and catalyst separated by simple filtration. After reaction course, catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence ecofriendly. Synthesized benzoins and acyloins by this method have been characterized on the basis of melting point and 1H-NMR spectral studies. Graphic Abstract: [Figure not available: see fulltext.]
Study on the reactivity of aldehydes in electrolyzed ionic liquids: Benzoin condensation - Volatile organic compounds (VOCs) vs. room temperature ionic liquids (RTILs)
Chiarotto,Feroci,Orsini,Feeney,Inesi
, p. 3287 - 3292 (2010)
The benzoin condensation of aromatic and heteroaromatic aldehydes, catalyzed by electrochemically generated N-heterocyclic carbenes, has been set up in the absence of organic solvents and bases. α-Hydroxy ketones have been isolated in good to elevated yields, in short reaction times. Aldol products and carbene-aldehyde adducts have been obtained in elevated yields from linear and short branched aldehydes, respectively. A comparison with the use of classical organic solvents has been reported Copyright
Partial reduction of α-diketones by sodium hydrogen selenide
Qiu,Chen,Zhang,Zhou
, p. 1529 - 1534 (1992)
α-Diketones can be partially reduced to the corresponding α-hydroxyketones by sodium hydrogen selenide in the presence of acetic acid, under mild conditions and in high yields.
Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes
Papadaki, Evanthia,Magrioti, Victoria
, (2020)
N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well as standalone organocatalysts in various reactions, mostly using aromatic aldehydes as substrates. We have previously demonstrated the efficiency of azolium-2-carboxylate zwitterions in the hydroxymethylation of aldehydes, especially aliphatic aldehydes, under microwave irradiation. In the present work, we report a series of pentafluorobenzene-based NHC adducts and their efficiency in the hydroxymethylation and self-condensation of aliphatic and aromatic aldehydes using microwave irradiation. The free carbenes are released under the reaction conditions and 1,3-dimesityl-2-(perfluorophenyl)imidazolidine and 1,3-bis(2,6-dimethylphenyl)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts.
Direct Formation of Benzoins from Diarylmethanones via a Rearrangement Reaction Promoted by Samarium Metal in DMF
Liu, Yongjun,Xu, Xiaoliang,Zhang, Yongmin
, p. 445 - 448 (2004)
Diarylmethanones react readily with DMF when promoted by samarium metal in DMF with TMSCl or iodine as an activator, to afford benzoins in good to excellent yields via rearrangement of aryl groups. As for asymmetric diarylmethanones, products resulting from the migration of either aryl group were obtained, where the migration of aryl groups shows certain priority.
One-step assembly of functionalized γ-butyrolactones from benzoins or benzaldehydes via an N-heterocyclic carbene-mediated tandem reaction
Ye, Wei,Cai, Guanliang,Zhuang, Zeyang,Jia, Xueshun,Zhai, Hongbin
, p. 3769 - 3771 (2005)
(Chemical Equation Presented) We describe here a direct, efficient, one-step construction of γ,γ-difunctionalized γ-butyrolactones from benzoins or benzaldehydes via a tandem reaction promoted by 1,3-dimethyl imidazolin-2-ylidene, an N-heterocyclic carbene (NHC).
Poly(4-vinylimidazolium) iodides: A highly recyclable organocatalyst precursor for benzoin condensation reaction
Seo, Ue Ryung,Chung, Young Keun
, p. 32371 - 32374 (2014)
The development of highly efficient, recyclable poly(4-vinylimidazolium) iodides (2) for the benzoin condensation reaction under mild reaction conditions is discussed: poly(4-vinyl N-heterocyclic carbene)s (3) obtained from 2 showed higher catalytic activity than monomeric 4-vinyl N-heterocyclic carbene and could be successfully recovered and reused over seven times without loss of performance. the Partner Organisations 2014.
An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation
Enders, Dieter,Kallfass, Ulrike
, p. 1743 - 1745 (2002)
The chiral bicyclic triazolium salt 1 is currently the most efficient precatalyst for the asymmetric benzoin condensation. The substituted acyloins 3 are obtained in moderate to good yields and with very good enantiomeric excesses from the corresponding aldehydes 2. The high asymmetric induction is presumably based on the conformational rigidity of the bicyclic nucleophilic carbene catalyst and on the steric hindrance of the tert-butyl group in the Breslow intermediate.
A New Class of Benzoin Condensation Catalyst, the Bi-(1,3-dialkylimidazolidin-2-ylidenes)
Lappert, Michael F.,Maskell, Robin K.
, p. 580 - 581 (1982)
An electron-rich olefin is an effective catalyst (at 1 molar percent concentration) for the benzoin condensation in aprotic non-polar media; the appropriate 2-aroylimidazolidine is obtained at high dilution under stoicheiometric conditions (olefin + 2ArCHO).
