4444-91-1Relevant articles and documents
Reissert-type acylation with acylzirconocene chloride complexes
Saito, Akio,Sakurai, Hikaru,Sudo, Kohei,Murai, Kosuke,Hanzawa, Yuji
, p. 7295 - 7299 (2013)
In the presence of ClCO2Et, the use of CuI in MeNO2 efficiently catalyzed the Reissert-type acylation of isoquinoline derivatives with acylzirconocene chlorides. In the reaction of quinolines with acylzirconocene chlorides, the choic
Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones
Vu, Nam Duc,Guicheret, Boris,Duguet, Nicolas,Métay, Estelle,Lemaire, Marc
supporting information, p. 3390 - 3399 (2017/07/28)
Herein, the preparation of methyl oleate α-hydroxyketone from the corresponding 1,2-diol was investigated using both homogeneous and heterogeneous systems. Homogeneous conditions using a Pd(OAc)2/neocuproine complex were first developed using oxygen as a sole oxidant under mild conditions (MeOH, 50 °C). Under these conditions, the conversion of diol reached 95%, and α-hydroxyketone was obtained with 97% selectivity. The access to α-hydroxyketone has also been studied by dehydrogenation using a range of heterogeneous catalysts under solvent-free conditions at high temperatures (160-180 °C). Dehydrogenation using activated Ru/C under vacuum provided α-hydroxyketone with 93% conversion and 82% GC yield. The optimized conditions were applied to a range of oleochemical diols, including a vegetable oil derivative, to obtain the corresponding α-hydroxyketones with up to 74% isolated yields.
Tandem hydroformylation/acyloin reaction - The synergy of metal catalysis and organocatalysis yielding acyloins directly from olefins
Ostrowski, Karoline A.,Fassbach, Thiemo A.,Vorholt, Andreas J.
supporting information, p. 1374 - 1380 (2015/07/07)
A novel, atom efficient, orthogonal tandem catalysis was developed yielding acyloin products (α-hydroxy ketones) directly from olefins under hydroformylation conditions. The combination of a metal-catalysed hydroformylation and an organocatalysed acyloin reaction provides three atom efficient C-C bond formations to linear, multifunctional molecules via linkage of the intermediate n-aldehydes. Additionally, the rhodium catalyst system gives a high n/bra ratio with an exclusive conversion of the terminal double bond in the hydroformylation and the n-aldehydes are converted selectively to their acyloins.