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Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids
Alternative Title银催化的脂肪酸脱羧氯代
Wang ZT(王振涛); Zhu L(朱林); Yin F(尹锋); Su ZQ(苏中全); Li ZD(李兆栋); Li CZ(李超忠)
Source PublicationJ. Am. Chem. Soc.
AbstractDecarboxylative 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.
Subject Area金属有机化学
Department中科院上海有机化学研究所; 中国科技大学
Indexed BySCI
WOS IDWOS:000301550800064
Citation statistics
Cited Times:158[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorLi CZ(李超忠)
Recommended Citation
GB/T 7714
Wang ZT,Zhu L,Yin F,et al. Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids[J]. J. Am. Chem. Soc.,2012,134(9):4258-4263.
APA 王振涛,朱林,尹锋,苏中全,李兆栋,&李超忠.(2012).Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids.J. Am. Chem. Soc.,134(9),4258-4263.
MLA 王振涛,et al."Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids".J. Am. Chem. Soc. 134.9(2012):4258-4263.
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