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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†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-05 00:00:00 , DOI: 10.1039/c8ob01095a
Zhengjiang Fu 1, 2, 3, 4, 5 , Ligao Jiang 1, 2, 3, 4 , Qianming Zuo 1, 2, 3, 4 , Zhaojie Li 1, 2, 3, 4 , Yanzhu Liu 1, 2, 3, 4 , Zhenhong Wei 1, 2, 3, 4 , Hu Cai 1, 2, 3, 4
Affiliation  

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.

中文翻译:

廉价的NaX(X = I,Br,Cl)作为有氧条件下实际的Ag / Cu介导的芳基羧酸脱羧卤化反应中的卤素供体

在好氧条件下,中等到良好的收率已经实现了易于获得的芳基羧酸与丰富的NaX(X = I,Br,Cl)之间的多功能且实用的Ag / Cu介导的脱羧卤化反应。对于在位具有硝基,氯和甲氧基取代基的含S的杂芳族羧酸和苯甲酸,表明卤代羧化是一种有效的策略。已经进行了克级反应和三步合成iniparib的过程,以评估该协议的实用性。初步的机械研究表明,Cu起着至关重要的作用,并且自由基途径参与了转变。
更新日期:2018-07-05
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