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Issue 30, 2018
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Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

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Abstract

Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.

Graphical abstract: Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

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Publication details

The article was received on 10 May 2018, accepted on 03 Jul 2018 and first published on 05 Jul 2018


Article type: Communication
DOI: 10.1039/C8OB01095A
Citation: Org. Biomol. Chem., 2018,16, 5416-5421
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    Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

    Z. Fu, L. Jiang, Q. Zuo, Z. Li, Y. Liu, Z. Wei and H. Cai, Org. Biomol. Chem., 2018, 16, 5416
    DOI: 10.1039/C8OB01095A

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