81113-20-4Relevant academic research and scientific papers
Method for synthesizing 1 - naphthol compound based on electrochemical intermolecular cyclization
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Paragraph 0013-0018, (2021/03/06)
The invention discloses a method for synthesizing a 1-naphthol compound based on electrochemical intermolecular cyclization. According to the method, a 1,3-dicarbonyl compound and alkyne are used forconducting an intermolecular cyclization reaction, the h
Photoredox Catalysis of Aromatic β-Ketoesters for in Situ Production of Transient and Persistent Radicals for Organic Transformation
Chen, Bin,Feng, Ke,Guo, Jia-Dong,Tung, Chen-Ho,Wu, Li-Zhu,Xiao, Hongyan,Yang, Xiu-Long
supporting information, p. 5365 - 5370 (2020/02/28)
Radical formation is the initial step for conventional radical chemistry. Reported herein is a unified strategy to generate radicals in situ from aromatic β-ketoesters by using a photocatalyst. Under visible-light irradiation, a small amount of photocatalyst fac-Ir(ppy)3 generates a transient α-carbonyl radical and persistent ketyl radical in situ. In contrast to the well-established approaches, neither stoichiometric external oxidant nor reductant is required for this reaction. The synthetic utility is demonstrated by pinacol coupling of ketyl radicals and benzannulation of α-carbonyl radicals with alkynes to give a series of highly substituted 1-naphthols in good to excellent yields. The readily available photocatalyst, mild reaction conditions, broad substrate scope, and high functional-group tolerance make this reaction a useful synthetic tool.
Electrochemical Synthesis of 1-Naphthols by Intermolecular Annulation of Alkynes with 1,3-Dicarbonyl Compounds
He, Mu-Xue,Mo, Zu-Yu,Wang, Zi-Qiang,Cheng, Shi-Yan,Xie, Ren-Ren,Tang, Hai-Tao,Pan, Ying-Ming
supporting information, p. 724 - 728 (2020/01/31)
C-centered radical cyclization under electrochemical conditions is a feasible strategy for constructing cyclic structures. Reported herein is the electrochemical synthesis of highly functionalized 1-naphthols using alkynes and 1,3-dicarbonyl compounds by
Mn(III)-Mediated Facile Access to Polysubstituted α-Naphthols from β-Keto Ester Derivatives and Terminal Alkynes
He, Lisheng,Yang, Yuzhu,Li, Fei,Liu, Xiaolan,Pan, Weidong
, p. 1959 - 1968 (2020/07/13)
A novel manganese-mediated reaction for the synthesis of polysubstituted α-naphthols has been developed from β-keto esters and terminal alkynes. This system holds the advantages of readily available starting materials and mild conditions. Mechanistic investigations revealed that this reaction proceeds via a tandem radical cyclization process.
Hantzsch Ester-Mediated Benzannulation of Diazo Compounds under Visible Light Irradiation
Nagode, Savita B.,Kant, Ruchir,Rastogi, Namrata
supporting information, p. 6249 - 6254 (2019/08/26)
A metal-free benzannulation of diazo compounds under visible light irradiation was developed. The photocatalytic single electron transfer by Hantzsch ester to the diazo enolates results into enolate vinyl radicals, which were trapped by alkynes leading to
Bromide-Mediated C-H Bond Functionalization: Intermolecular Annulation of Phenylethanone Derivatives with Alkynes for the Synthesis of 1-Naphthols
Lu, Tao,Jiang, Ya-Ting,Ma, Feng-Ping,Tang, Zi-Jing,Kuang, Liu,Wang, Yu-Xuan,Wang, Bin
supporting information, p. 6344 - 6347 (2017/12/08)
Bromide-mediated intermolecular annulation of phenylethanone derivatives with alkynes has been developed, which allows for the regioselective formation of polysubstituted 1-naphthols. The usage of readily available bromine catalyst, broad substrate scope, and mild conditions make this protocol very practical. Mechanistic investigations reveal that the bromination of phenylethanone derivatives occurs to yield bromo-substituted intermediates, which react in situ with alkynes to furnish the desired 1-naphthols.
Synthesis method of polysubstituted 1-naphthol and derivatives thereof
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Paragraph 0041; 0042; 0043; 0044, (2016/10/09)
The invention provides a synthesis method of polysubstituted 1-naphthol and derivatives thereof. The synthesis method is characterized in that alkyne and 1,3-dicarbonyl compound are used as raw materials, and polysubstituted 1-naphthol and derivatives the
Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products
Naresh, Gunaganti,Kant, Ruchir,Narender, Tadigoppula
supporting information, p. 3446 - 3449 (2015/07/28)
A novel route has been developed for regioselective synthesis of highly substituted α-naphthols, binaphthols, and anthracenol through silver(I) catalyzed C(sp3)-H/C(sp)-H, C(sp2)-H/C(sp)-H functionalization of β-ketoesters and alkyne
De Novo synthesis of polysubstituted naphthols and furans using photoredox neutral coupling of alkynes with 2-bromo-1,3-dicarbonyl compounds
Jiang, Heng,Cheng, Yuanzheng,Zhang, Yan,Yu, Shouyun
supporting information, p. 4884 - 4887 (2013/10/08)
A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.
Selenium-mediated synthesis of biaryls through rearrangement
Shahzad, Sohail A.,Vivant, Clotilde,Wirth, Thomas
supporting information; experimental part, p. 1364 - 1367 (2010/06/17)
"Chemical Equation Presented" A new cyclization of β-keto ester substituted stilbene derivatives using selenium electrophiles in the presence of Lewis acids is described. Substituted naphthols are obtained through cyclization and subsequent 1,2-rearrangement of aryl groups under very mild reaction conditions.
