75391-07-0Relevant articles and documents
A simple iron-catalyst for alkenylation of ketones using primary alcohols
Sk, Motahar,Kumar, Ashish,Das, Jagadish,Banerjee, Debasis
, (2020/04/10)
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.
Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure
Ardanaz, Sebastián M.,Borucki, Estefanía L.,Velez Rueda, Ana J.,Parisi, Gustavo,Iribarren, Adolfo M.,Iglesias, Luis E.
, p. 50 - 57 (2019/08/26)
Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde which provided high conversions (77–95%) of the corresponding enones (isolated in a range of yields from 19% to 74%). Parameters assayed to achieve these conversion values were solvent, ketone/aldehyde molar ratio and temperature. In this procedure only cyclohexanone gave the bis-enone, by-product of the conventional aldol condensation, in low amount even at high benzaldehyde/cyclohexanone molar excess. Under the assayed conditions null or low ketol amounts were observed, except for the reaction of cyclopentanone and p-nitrobenzaldehyde. Moreover, kinetic data of BSA-catalysed aldol condensation of cyclohexanone and p-nitrobenzaldehyde suggest an ordered bi bi mechanism for enone formation; an enamine mechanism involving residues of the catalytic cavity exhibiting abnormal pKa values is also proposed.
Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster
Wu, Yufei,Hou, Jie,Liu, Yuliang,Zhang, Mingfu,Tung, Chen-Ho,Wang, Yifeng
, p. 1511 - 1516 (2016/03/01)
The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.
