- Visible light-mediated transition metal-free esterification of amides with boronic acids
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A novel strategy for visible light-mediated esterification of amides with boronic acids in air has been described. This method is characterized by mild reaction conditions and low cost owing to no need of any catalyst, which implies high potential utility in late-stage functionalization of amide drugs and materials.
- Ding, Hao,Qi, Wan-Ying,Zhen, Jing-Song,Ding, Qiuping,Luo, Yong
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supporting information
(2020/10/02)
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- Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights
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Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).
- Li, Li,Song, Feifei,Zhong, Xiumei,Wu, Yun-Dong,Zhang, Xinhao,Chen, Jiean,Huang, Yong
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supporting information
p. 126 - 132
(2019/11/28)
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- Method for preparing carboxylate aryl type compound
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The invention belongs to the field of drug synthesis and in particular relates to a method for preparing a carboxylate aryltype compound. The preparation method provided by the invention comprises thefollowing steps: providing a compound A of a formula a shown in the description, a compound B of a formula b shown in the description, an organic palladium complex, and a silver salt, wherein the organic palladium complex is composed of a palladium compound and a nitrogen-containing ligand; the nitrogen-containing ligand comprises an o-phenoline compound and/or a bipyridine compound; and mixing the compound A, the compound B, the organic palladium complex and the silver salt in a reaction solvent, and performing a reaction in an inert gas atmosphere, so as to obtain the carboxylate aryl typecompound of a formula I shown in the description. As the organic palladium complex and the silver salt are simultaneously used, direct selectivity C-O coupling of carboxylic acid and halogenated aromatic hydrocarbon is realized, and the method is applicable to a variety of carboxylic acid substrates and halogenated aromatic substrates, and is wide in compatibility and high in yield.
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Paragraph 0135-0140
(2020/02/10)
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- Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents
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A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.
- Shih, Bo-Hao,Basha, R. Sidick,Lee, Chin Fa
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p. 8862 - 8866
(2019/09/30)
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- Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols
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In this report, we have developed a sustainable protocol for the synthesis of aromatic esters by a carbonylative method using di-μ-chlorobis [5-hydroxy-2-[1-(hydroxyimino-?N) ethyl] phenyl-?C] palladium (II) dimer (1) catalyst in PEG-400 as a greener and recyclable solvent. The reaction is carried out at room temperature using CO in a balloon. Good to excellent yield of various esters can be synthesize using this protocol. Direct insertion of CO moiety leads to the high atom and step economy. Compared to previous protocol this phosphine free approach for the synthesis of aromatic esters provides high Turnover Number (TON) and Turnover Frequency (TOF). Developed approach has an alternative route for use of conventional palladium precursor with high conversion and selectivity. The catalyst system and product can easily be separated using diethyl ether as a solvent. The Pd/PEG-400 system could be reused up to a fifth consecutive cycle without any loss of its activity and selectivity.
- Gaikwad, Vinayak V.,Bhanage, Bhalchandra M.
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- Electrodimerization of N-Alkoxyamides for Zinc(II) Catalyzed Phenolic Ester Synthesis under Mild Reaction Conditions
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An electrochemical On-Off method for phenolic ester synthesis from N-alkoxyamides has been reported. This one-pot protocol begins with rapid and selective electrodimerization of the amide using n-Bu4NI (TBAI) as an electrocatalyst. The reaction proceeds further in the absence of current via Zn catalyzed C?N bond activation of the amide dimer followed by its coupling with phenol to form the ester. The present methodology is ligand-free and takes place under mild reaction conditions. This transformation incorporates a wide variety of phenols and amide substrates leading to the formation of functionalized esters highlighting its versatility. (Figure presented.).
- Subramanian, Kripa,Yedage, Subhash L.,Bhanage, Bhalchandra M.
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p. 2511 - 2521
(2018/05/14)
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- Pd/C catalyzed phenoxycarbonylation using: N -formylsaccharin as a CO surrogate in propylene carbonate, a sustainable solvent
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This work reports the first Pd/C catalyzed phenoxycarbonylation of aryl iodides using N-formylsaccharin as a CO surrogate. Advantageously, the reaction could be carried out in propylene carbonate, an environmentally benign and sustainable polar aprotic solvent under CO surrogacy. Using N-formylsaccharin as a CO surrogate allows the usage of cheaper and readily available phenols as the coupling partner. A range of phenyl esters could be synthesized under mild, co-catalyst free, ligand free and additive free conditions, including multi-substituted novel phenyl esters. The Pd/C catalyst could be recycled up to four times with only a slight loss in activity. The reaction could be scaled up to gram scale synthesis.
- Gautam, Prashant,Kathe, Prasad,Bhanage, Bhalchandra M.
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supporting information
p. 823 - 830
(2017/08/15)
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- Metal-free synthesis of aryl esters by coupling aryl carboxylic acids and aryl boronic acids
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A facile synthesis of aryl esters is developed by coupling aryl carboxylic acids and aryl boronic acids in the presence of PhI(OAc)2 and carbonyl diimidazole. A wide range of functional groups were tolerant to the metal-free reaction condition that led to the desired products in good yields.
- Ruso, Jayaraman Sembian,Rajendiran, Nagappan,Kumaran, Rajendran Senthil
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supporting information
p. 2345 - 2347
(2014/05/06)
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- ORTHO - PHENYLPHENOL COMPOUNDS USEFUL AS HYDROCARBON MARKERS
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A compound having formula (I), wherein G1 represents a C4-C22 alkyl or alkenyl group, a C8-C20 aralkyl group or formula (II) wherein G3 is a difunctional C2-C18 alkyl or alkenyl group, a difunctional C6-C20 aryl group or G3 is absent; provided that G1 is not 2-butyl, n-hexyl, n-octyl, n-dodecyl, n-hexadecyl or 2- phenylethyl.
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Page/Page column 8
(2012/12/13)
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