Hunsdiecker Reaction

The silver(I) salts of carboxylic acids react with halogens to give unstable intermediates which readily decarboxylate thermally to yield alkyl halides. The reaction is believed to involve homolysis of the C-C bond and a radical chain mechanism.

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Mechanism of the Hunsdiecker Reaction

Recent Literature

Metal-Free Efficient, General and Facile Iododecarboxylation Method with Biodegradable Co-Products
K. Kulbitski, G. Nisnevich, M. Gandelman, Adv. Synth. Catal., 2011, 353, 1438-1442.

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.

Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids
Z. Wang, L. Zhu, F. Yin, Z. Su, Z. Li, C. Li, J. Am. Chem. Soc., 2012, 134, 4258-4263.

Catalytic Hunsdiecker Reaction of α,β-Unsaturated Carboxylic Acids: How Efficient Is the Catalyst?
J. Prakash, S. Roy, J. Org. Chem., 2002, 67, 7861-7864.

Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced Hunsdiecker-Type Reaction
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Synthesis, 2005, 1319-1325.