Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids

Zhentao Wang, Lin Zhu, Feng Yin, Zhongquan Su, Zhaodong Li and Chaozhong Li*

*Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China, Email: cligmail.sioc.ac.cn

Z. Wang, L. Zhu, F. Yin, Z. Su, Z. Li, C. Li, J. Am. Chem. Soc., 2012, 134, 4258-4263.

DOI: 10.1021/ja210361z

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Abstract

An efficient, catalytic Hunsdiecker reaction of aliphatic carboxylic acids affords the corresponding chlorodecarboxylation products in high yields under mild conditions in the presence of t-butyl hypochlorite and Ag(Phen)₂OTf as catalyst. The reaction exhibits remarkable functional group compatibility.

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proposed mechanism

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Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids

X. Tan, T. Song, Z. Wang, H. Chen, L. Cui, C. Li, Org. Lett., 2017, 19, 1634-1637.

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Key Words

Hunsdiecker Reaction, Alkyl Chlorides, Benzyl Chlorides, t-butyl hypochlorite

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ID: J48-Y2012-0700