Employment of a C(sp3)-based nucleophile for photoinduced palladium-catalysed cross-coupling

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-06-11 DOI:10.1039/d5sc02325d

Beom Ho Kim, Byeongdo Roh, Dong Jun Kim, Hong Geun Lee

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Abstract

The development of efficient methods for C(sp³)–C(sp³) bond formation remains a longstanding challenge in synthetic chemistry, especially in palladium catalysis employing sterically bulky electrophiles. In this study, we present a novel approach for achieving C(sp³)–C(sp³) cross-coupling via photoinduced palladium catalysis, employing cyclopropanols as masked C(sp³)-nucleophiles. Leveraging the unique reactivity of photoexcited palladium, this protocol enables radical-mediated C(sp³)–C(sp³) coupling across a broad range of substrates including sterically hindered and functionally diverse alkyl halides under mild conditions. This method significantly expands the extent of palladium-catalysed cross-coupling for bond construction between sp³-hybridized carbon units, providing streamlined access to structurally complex C(sp³)-rich frameworks that are crucial for medicinal chemistry.

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C（sp3）基亲核试剂在光诱导钯催化交叉偶联中的应用

开发C(sp3) -C （sp3）键形成的有效方法仍然是合成化学中长期存在的挑战，特别是在使用空间体积大的亲电试剂催化钯方面。在这项研究中，我们提出了一种通过光诱导钯催化实现C(sp3) -C （sp3）交叉偶联的新方法，利用环丙醇作为掩膜C(sp3)-亲核试剂。利用光激发钯的独特反应活性，该方案使自由基介导的C(sp3) -C （sp3）偶联能够在温和条件下跨越广泛的底物，包括空间阻碍和功能多样化的烷基卤化物。该方法极大地扩展了钯催化的sp3杂化碳单元之间的交叉偶联键构建的范围，为结构复杂的富含C（sp3）的框架提供了简化的途径，这对药物化学至关重要。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.