19434-30-1Relevant 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.
Water-Tolerant ortho-Acylation of Phenols
Dong, Shuang-Feng,Gao, Zhi-Yuan,He, Yu,Liu, Xu,Loh, Teck-Peng,Tian, Jie-Sheng,Wu, Peng
, p. 6594 - 6598 (2021/09/02)
A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.
Eco-friendly organocatalyst- And reagent-controlled selective construction of diverse and multifunctionalized 2-hydroxybenzophenone frameworks for potent UV-A/B filters by cascade benzannulation
Akhtar, Muhammad Saeed,Inductivo Tamargo, Ramuel John,Kim, Sung Hong,Lee, Yong Rok,Thombal, Raju S.,Yang, Won-Guen
supporting information, p. 4523 - 4531 (2020/08/10)
The organocatalyst- and reagent-controlled highly selective synthesis of diversely functionalized novel 2-hydroxybenzophenone frameworks, such as 2-hydroxy-3′-formylbenzophenones, 7-(2′-hydroxybenzoyl)-2-naphthaldehydes, and 2-hydroxybenzophenones, under green conditions, for the development of potent UV-A/B filters is described. The organocatalyzed benzannulation reactions proceed individually via [3 + 3] cycloaddition for the synthesis of 2-hydroxy-3′-formylbenzophenones and [4 + 2] cycloaddition for 2-hydroxybenzophenones. With this methodology, an unprecedented double benzannulation allows one-pot construction of diverse 7-(2′-hydroxybenzoyl)-2-naphthaldehydes via [3 + 3 + 4] cycloaddition. This protocol features a broad substrate scope, high functional-group tolerance, and operational simplicity in an environmentally benign green solvent. The synthesized compounds are successfully utilized for further transformations and well characterized as potent UV-A/B filters.
Efficient visible-light photocatalytic aerobic oxidation of cyclic sulfamides to imines
Ming, Zong-Yao,Li, Kang-Rui,Meng, Fan-Jie,Shi, Lei,Jiang, Wen-Feng
supporting information, (2020/06/17)
A highly efficient photocatalytic aerobic oxidation of cyclic sulfamides to synthesize cyclic N-sulfonyl imines with Ir(ppy)2(dtbpy)PF6 as photocatalyst is reported. These environmentally friendly transformations exihibit good to excellent isolated yields and good generality with respect to both five-membered and six-membered cyclic sulfamides.
Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
Hu, Le' an,Zhang, Yao,Zhang, Qing-Wen,Yin, Qin,Zhang, Xumu
, p. 5321 - 5325 (2020/02/28)
A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.
Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
Prasanna Kumari, Subramaniyan,Suresh, Pavithira,Muthukumar, Vijayashree,Selva Ganesan, Subramaniapillai
supporting information, (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.
Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information, p. 12724 - 12729 (2019/11/05)
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Efficient catalytic synthesis method of 2-hydroxybenzophenone compound
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Paragraph 0017; 0018, (2019/04/11)
The invention discloses a 2-hydroxybenzophenone compound and a green catalytic synthesis method thereof. According to the method, under the conditions of using coumaranone and coumaranone derivativesas raw materials, using nickel chloride as a catalyst, using methylbenzene as a solvent, using di-tert-butyl peroxide as an oxidizing agent, and using sodium carbonate as alkali, the 2-hydroxybenzophenone compound is obtained at high yield. The method has the advantages that the cost is low; the yield is high; the operation is simple and convenient; no pollution is caused and the like. The potential industrial application prospects are realized. The method provides a cheap and green path for the preparation of the 2-hydroxybenzophenone compound.
Integrating Metal-Catalyzed C-H and C-O Functionalization to Achieve Sterically Controlled Regioselectivity in Arene Acylation
Serratore, Nicholas A.,Anderson, Constance B.,Frost, Grant B.,Hoang, Truong-Giang,Underwood, Steven J.,Gemmel, Philipp M.,Hardy, Melissa A.,Douglas, Christopher J.
supporting information, p. 10025 - 10033 (2018/07/21)
One major goal of organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation is the most renowned method for the synthesis of aryl ketones, a common structural motif of many pharmaceuticals, agrochemicals, fragrances, dyes, and other commodity chemicals. However, an EAS synthetic strategy is only effective if the desired site for acylation is in accordance with the electronic-controlled regioselectivity of the reaction. Herein we report steric-controlled regioselective arene acylation with salicylate esters via iridium catalysis to access distinctly substituted benzophenones. Experimental and computational data indicate a unique reaction mechanism that integrates C-O activation and C-H activation with a single iridium catalyst without an exogenous oxidant or base. We disclose an extensive exploration of the synthetic scope of both the arene and the ester components, culminating in the concise synthesis of the potent anticancer agent hydroxyphenstatin.
One-pot synthesis of ortho-acylphenols by palladium-catalyzed phenol C–H addition to nitriles
Jiang, Tao-Shan,Gan, Bei,Wang, Xi,Zhang, Xiuli
supporting information, p. 4197 - 4199 (2017/10/06)
The regioselective one-pot synthesis of ortho-acylphenols via the palladium-catalyzed addition of phenols to nitriles and subsequent hydrolysis is reported. The acylation reaction proceeded smoothly using the Pd(OAc)2/DMSO system and TFA as the additive. This method also provides a direct strategy for the synthesis of a salicylketoxime scaffold.
