Synthesis of Polysubstituted Aromatics via the Pd(II)-Initiated Borono-Catellani Reaction

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-06 DOI:10.1021/acs.orglett.5c00503
Wangyang Li, Yong Lu, Shanshan Cheng, Qiuling Song
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Abstract

Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc)2 and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.

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Pd(II)引发的硼- catellani反应合成多取代芳烃
在此,我们报道了一种新的钯(II)引发的硼- catellani反应,该反应首次利用广泛可及的芳基硼酸作为反应的起始底物和终止底物。以空气为氧化剂,Pd(OAc)2和NBE协同催化硼- catellani反应,为新型catellani反应开辟了新的场所。重要的是,该方法在这些环境友好和温和的反应条件下与广泛的底物兼容,包括萘硼酸、苯基硼酸衍生物、烷基碘化物和芳基碘化物,从而证明了多功能官能团相容性,可用于合成有价值的多取代芳烃。
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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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