Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c01269

Yingjun Lan, Siqi Xie, Bin Liu

引用次数: 0

Abstract

Aryl chlorides are more commercially available and lower cost compared with aryl bromides and iodides. However, the use of (hetero)aryl chlorides as aryl radical precursors for the di(hetero)arylation of alkenes remains an underdeveloped area. Furthermore, existing examples of theses reactions are predominantly confined to activated alkenes. In this study, we introduce a photoirradiation-promoted benzophenone-catalyzed 1,2-di(hetero)arylation process that is applicable to both activated and unactivated alkenes, utilizing (hetero)aryl chlorides and cyanoarenes as aryl sources. Importantly, this method allows for the simultaneous introduction of two heterocycles to alkenes with high regioselectivity.

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活化和未活化烯烃与（杂）芳基氯化物的区域选择性1,2-二（杂）芳基化

与芳基溴化物和碘化物相比，芳基氯化物在商业上更容易获得，成本更低。然而，利用（杂）芳基氯化物作为芳基前体进行烯二（杂）芳基化反应仍然是一个不发达的领域。此外，这些反应的现有例子主要局限于活化烯烃。在这项研究中，我们介绍了一种光照射促进二苯甲酮催化的1,2-二（杂）芳基化工艺，该工艺适用于活化和未活化的烯烃，利用（杂）芳基氯化物和氰芳烃作为芳基源。重要的是，该方法允许在烯烃上同时引入两个杂环，具有很高的区域选择性。

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来源期刊

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.