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Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids
其他题名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)
2012
发表期刊J. Am. Chem. Soc.
ISSN0002-7863
卷号134期号:9页码:4258-4263
摘要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.
学科领域金属有机化学
部门归属中科院上海有机化学研究所; 中国科技大学
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收录类别SCI
语种英语
WOS记录号WOS:000301550800064
引用统计
被引频次:141[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28015
专题金属有机化学国家重点实验室
通讯作者Li CZ(李超忠)
推荐引用方式
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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