6333-07-9Relevant academic research and scientific papers
Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids
Xiao, Lin,Lang, Tao-Tao,Jiang, Ying,Zang, Zhong-Lin,Zhou, Cheng-He,Cai, Gui-Xin
supporting information, p. 3278 - 3283 (2021/02/01)
We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.
Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
Prasanna Kumari, Subramaniyan,Suresh, Pavithira,Muthukumar, Vijayashree,Selva Ganesan, Subramaniapillai
, (2020/10/13)
A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.
I-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions
Colas, Kilian,Dos Santos, A. Catarina V. D.,Mendoza, Abraham
supporting information, (2019/10/08)
The direct preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.
Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions
Tran, Phuong Hoang,Phung, Huy Quang,Duong, Minh Nhat,Pham-Tran, Nguyen-Nguyen
supporting information, p. 1558 - 1563 (2017/04/03)
An efficient and simple route for the synthesis of ortho-hydroxyaryl ketones has been developed. The microwave-assisted direct C-benzoylation of phenols and naphthols in the presence of metal triflates afforded the corresponding ortho-hydroxyaryl ketones in moderate to excellent yields. Bismuth triflate showed the best catalytic performance compared to other metal triflates. The protocol has advantages including short reaction times, high chemoselectivity towards C-acylation, and simple work-up. Additionally, bismuth triflate can be easily recovered and reused several times without significant loss of catalytic performance.
Copper catalyzed oxidative deamination of Betti bases: An efficient approach for benzoylation/formylation of naphthols and phenols
Deb, Mohit L.,Pegu, Choitanya Dev,Borpatra, Paran J.,Baruah, Pranjal K.
, p. 40552 - 40559 (2016/05/24)
An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.
Synthesis of 2-acylphenol and flavene derivatives from the ruthenium-catalyzed oxidative c-h acylation of phenols with aldehydes
Lee, Hanbin,Yi, Chae S.
supporting information, p. 1899 - 1904 (2015/03/18)
The cationic ruthenium hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- has been found to be an effective catalyst for the oxidative C-H coupling reaction of phenols with aldehydes to give 2-acylphenol compounds. The coupling of phenols with α,β-unsaturated aldehydes selectively gives the flavene derivatives. The catalytic method mediates direct oxidative C-H coupling of phenol and aldehyde substrates without using any metal oxidants or forming wasteful byproducts. A cationic ruthenium hydride complex catalyzes the oxidative C-H coupling of phenols with aldehydes to form 2-acylphenol and flavene derivatives.
Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
Wang, Dahai,Cui, Sunliang
, p. 8511 - 8516 (2016/01/25)
A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.
Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions
Gaikwad, Sunil V.,Nawghare, Beena R.,Lokhande, Pradeep D.
, p. 319 - 325 (2015/07/27)
Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.
Copper-catalyzed regioselective intramolecular oxidative α-functionalization of tertiary amines: An efficient synthesis of dihydro-1,3-oxazines
Deb, Mohit L.,Dey, Suvendu S.,Bento, Isabel,Barros, M. Teresa,Maycock, Christopher D.
, p. 9791 - 9795 (2013/09/23)
Traffic control: The hydroxy functional group directs the α-functionalization of tertiary amines, synthesizing 1,3-oxazines by C-O bond formation. Reaction occurs with both benzylic and non-benzylic amines. In the case of naphthoxazine synthesis, 100 % diastereoselectivity was observed. A tentative two-pathway mechanism is proposed for the reaction. Copyright
Synthesis and biological activity of naphthyl-substituted (B-ring) benzophenone derivatives as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
Ma, Xiao-Dong,Zhang, Xuan,Dai, Hui-Fang,Yang, Shi-Qiong,Yang, Liu-Meng,Gu, Shuang-Xi,Zheng, Yong-Tang,He, Qiu-Qin,Chen, Fen-Er
experimental part, p. 4601 - 4607 (2011/09/19)
A novel series of benzophenone derivatives with B-ring substituted by naphthyl ring has been synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Most of these compounds showed good to moderate activity against wild-type HIV
