Cerium Ammonium Nitrate (CAN)-Promoted C(sp2)–N Coupling of Secondary Amides with Aryl Boronic Acids: Entries to Tertiary Aryl Amides

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-04-02 DOI:10.1021/acs.orglett.5c00108
Gaofeng Feng, Chao Zhang, Jing-Yao He, Tao Cai, Wenzhe Xu, Jian Jin
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Abstract

A cerium ammonium nitrate (CAN)-promoted C(sp2)–N coupling reaction of secondary amides with aryl boronic acids has been realized, providing a new entry for the construction of structurally diverse tertiary aryl amides, which are widely found in various biologically active molecules. Preliminary mechanistic studies indicated that a radical pathway may be involved in the C(sp2)–N coupling process. Compared with other metal-catalyzed methods, which in some cases require well-designed catalysts, preassembled directing groups, and/or complicated operations, this methodology features a ligand- and directing group-free process, as well as ease of handling.

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硝酸铈铵(CAN)-促进C(sp2) -N偶联仲酰胺与芳基硼酸:叔芳基酰胺的入口
硝酸铵铈(CAN)促进仲酰胺与芳基硼酸的C(sp2) -N偶联反应得以实现,为构建结构多样的叔芳基酰胺提供了新的途径,叔芳基酰胺广泛存在于各种生物活性分子中。初步的机制研究表明,C(sp2) -N偶联过程可能有一条自由基途径参与。其他金属催化方法在某些情况下需要精心设计的催化剂、预先组装的导向基团和/或复杂的操作,与之相比,这种方法的特点是不需要配体和导向基团,而且易于操作。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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