73408-30-7Relevant academic research and scientific papers
Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles
Zhang, Sheng,Yamamoto, Yoshinori,Bao, Ming
, p. 13981 - 13990 (2018/11/30)
The palladium-catalyzed reaction of 1-(chloromethyl)naphthalenes 1 with (hetero)arylacetonitriles 2 gives either para- or ortho-acylated naphthalenes (3 or 4) in good to high yields. The regioselectivity can be controlled by the ligand of a palladium catalyst. A sterically bulky ligand, tBuPPh2, affords para-acylated products 3, whereas a sterically less bulky ligand, Me2PPh, provides ortho-acylated products 4. Further, direct substitution product 5 at the benzylic position is not obtained essentially, although such a reaction at the benzylic position is favorable in ordinary nucleophilic substitutions. In this paper, it was revealed that the benzylpalladium intermediate could react through a different mode (η3-benzylpalladium intermediate or η1-benzylpalladium intermediate) in nucleophilic aromatic substitution. In addition to the interesting mechanistic aspect, the present reaction provides a facile synthetic method for a wide range of diaryl ketones, some of which are not easily available through the previously known procedures.
Preparation method of Alpha-naphthyl containing diarylketone compound
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Paragraph 0042-0043, (2017/07/01)
The invention belongs to the technical field of pharmaceutical chemical intermediates and related chemistry and provides a preparation method of Alpha-naphthyl containing diarylketone compound; the preparation method comprises: reacting, under the action of a metal catalyst, a ligand and an alkali, 1-(chloromethyl)naphthalene and its derivatives as materials with phenylacetonitrile compounds in an anhydrous organic solvent, and converting, under the action of an oxidant, into the Alpha-naphthyl containing diarylketone compound. The preparation method has the advantages that the synthetic route is short, the conditions are mild, operating is simple, it is probable to industrialize the method, the yield of diarylketone products is high, it is possible, on naphthalene rings of the diarylketone compound synthesized by using the method, to further functionalize methyl so that the functional molecules, such as drug intermediates, optical materials, are acquired.
