The Experts below are selected from a list of 303 Experts worldwide ranked by ideXlab platform
Feng Yin - One of the best experts on this subject based on the ideXlab platform.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
ChemInform, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Under catalysis of Ag(phen)2OTf, primary, secondary and tertiary aliphatic Carboxylic Acids are decarboxylated and chlorinated by tBuOCl.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
Journal of the American Chemical Society, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Decarboxylative halogenation of Carboxylic Acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic Carboxylic Acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic Carboxylic Acids. Thus, with the catalysis of Ag(Phen)(2)OTf, the reactions of Carboxylic Acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
Zhentao Wang - One of the best experts on this subject based on the ideXlab platform.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
ChemInform, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Under catalysis of Ag(phen)2OTf, primary, secondary and tertiary aliphatic Carboxylic Acids are decarboxylated and chlorinated by tBuOCl.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
Journal of the American Chemical Society, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Decarboxylative halogenation of Carboxylic Acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic Carboxylic Acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic Carboxylic Acids. Thus, with the catalysis of Ag(Phen)(2)OTf, the reactions of Carboxylic Acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
Zhenzhen Zhang - One of the best experts on this subject based on the ideXlab platform.
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silver catalyzed decarboxylative trifluoromethylation of aliphatic Carboxylic Acids
Journal of the American Chemical Society, 2017Co-Authors: Xinqiang Tan, Zhonglin Liu, Haigen Shen, Pei Zhang, Zhenzhen ZhangAbstract:The silver-catalyzed decarboxylative trifluoromethylation of aliphatic Carboxylic Acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic Carboxylic Acids with (bpy)Cu(CF3)3 (bpy = 2,2′-bipyridine) and ZnMe2 in aqueous acetonitrile at 40 °C afford the corresponding decarboxylative trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl Carboxylic Acids and exhibits wide functional group compatibility. Mechanistic studies reveal the intermediacy of –Cu(CF3)3Me, which undergoes reductive elimination and subsequent oxidation to give Cu(CF3)2 as the active species responsible for the trifluoromethylation of alkyl radicals.
Lin Zhu - One of the best experts on this subject based on the ideXlab platform.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
ChemInform, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Under catalysis of Ag(phen)2OTf, primary, secondary and tertiary aliphatic Carboxylic Acids are decarboxylated and chlorinated by tBuOCl.
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silver catalyzed decarboxylative chlorination of aliphatic Carboxylic Acids
Journal of the American Chemical Society, 2012Co-Authors: Zhentao Wang, Lin Zhu, Feng YinAbstract:Decarboxylative halogenation of Carboxylic Acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic Carboxylic Acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic Carboxylic Acids. Thus, with the catalysis of Ag(Phen)(2)OTf, the reactions of Carboxylic Acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
David W C Macmillan - One of the best experts on this subject based on the ideXlab platform.
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decarboxylative fluorination of aliphatic Carboxylic Acids via photoredox catalysis
ChemInform, 2015Co-Authors: Sandrine Ventre, Filip Petronijevic, David W C MacmillanAbstract:An operationally simple and mild protocol is developed for the conversion of a wide range of Carboxylic Acids into fluoroalkanes.
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decarboxylative fluorination of aliphatic Carboxylic Acids via photoredox catalysis
Journal of the American Chemical Society, 2015Co-Authors: Sandrine Ventre, Filip Petronijevic, David W C MacmillanAbstract:The direct conversion of aliphatic Carboxylic Acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of Carboxylic Acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.
