33663-73-9Relevant articles and documents
Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester: Via chemoselective C(acyl)-O bond activation
Ma, Hongpeng,Bai, Chaolumen,Bao, Yong-Sheng
, p. 17266 - 17272 (2019/06/24)
A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)-O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused and shows high activity after eight cycles. The XPS analysis of the catalyst before and after the reaction suggested that the reaction might be performed via a Pd0/PdII catalytic cycle that began with Pd0.
Diarylketone preparation method
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Paragraph 0019; 0032, (2017/09/05)
The invention discloses a diarylketone preparation method. According to the method, substituted nitrobenzene and aromatic acetic ester are dissolved in an organic solvent, alkali is added, the mixture is subjected to a reaction in the air or oxygen atmosphere at the temperature of 10-60 DEG C for 0.5-24 h, and diarylketone is obtained; the mole ratio of substituted nitrobenzene to aromatic acetic ester is (0.5:1)-(5:1), and the mole ratio of alkali to aromatic acetic ester is (1:1)-(5:1). The method overcomes defects caused by the adoption of strong acid or expensive metal reagents or strong oxidizers and the like in the prior art and has the advantages as follows: 1) with air as an oxidizer, use of strong or expensive chemical oxidizers is avoided; 2) no transition metal catalysts are used, so that the condition that heavy metal ions are left in a product is avoided; 3) without inductive groups, surplus steps of introduction of the inductive groups and removal of the inductive groups are avoided; 4) acylation of ortho positions or para positions of nitro-aromatic compounds is directly realized, which cannot be realized with a classic Friedel-Crafts acylation method. The synthesis method plays an important role in preparing diarylketone, particularly industrial production of acylation products of ortho positions or para positions of the nitro-aromatic compounds.
Highly diastereoselective arylation of (S)-mandelic acid enolate: Enantioselective synthesis of substituted (R)-3-hydroxy-3-phenyloxindoles and (R)-benzylic acids and synthesis of nitrobenzophenones
Barroso, Santiago,Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Garcia, Begona,Pedro, Jose R.
, p. 6821 - 6829 (2007/10/03)
An easy access to substituted (R)-3-hydroxy-3-phenyloxindoles, (R)-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2S,5S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several o- and p-halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the o-nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure (R)-3-hydroxy-3- phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted (R)-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives substituted nitrobenzophenones.
