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可见光诱导的烯烃的化学选择性1,2-二杂芳基化反应

Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.

作者信息

Guo Shi-Yu, Liu Yi-Peng, Huang Jin-Song, He Li-Bowen, He Gu-Cheng, Ji Ding-Wei, Wan Boshun, Chen Qing-An

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.

University of Chinese Academy of Sciences, Beijing, China.

出版信息

Nat Commun. 2024 Jul 19;15(1):6102. doi: 10.1038/s41467-024-50460-4.

Abstract

Visible-light photocatalysis has evolved as a powerful technique to enable controllable radical reactions. Exploring unique photocatalytic mode for obtaining new chemoselectivity and product diversity is of great significance. Herein, we present a photo-induced chemoselective 1,2-diheteroarylation of unactivated alkenes utilizing halopyridines and quinolines. The ring-fused azaarenes serve as not only substrate, but also potential precursors for halogen-atom abstraction for pyridyl radical generation in this photocatalysis. As a complement to metal catalysis, this photo-induced radical process with mild and redox neutral conditions assembles two different heteroaryl groups into alkenes regioselectively and contribute to broad substrates scope. The obtained products containing aza-arene units permit various further diversifications, demonstrating the synthetic utility of this protocol. We anticipate that this protocol will trigger the further advancement of photo-induced alkyl/aryl halides activation.

摘要

可见光光催化已发展成为一种实现可控自由基反应的强大技术。探索独特的光催化模式以获得新的化学选择性和产物多样性具有重要意义。在此,我们报道了利用卤代吡啶和喹啉对未活化烯烃进行光诱导化学选择性1,2 - 二杂芳基化反应。稠环氮杂芳烃不仅作为底物,而且在该光催化反应中还是用于生成吡啶基自由基的卤素原子提取的潜在前体。作为金属催化的补充,这种在温和且氧化还原中性条件下的光诱导自由基过程将两个不同的杂芳基选择性地组装到烯烃上,并具有广泛的底物范围。所得到的含氮杂芳烃单元的产物允许进行各种进一步的衍生化,证明了该方法的合成实用性。我们预计该方法将推动光诱导烷基/芳基卤化物活化的进一步发展。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de8/11271625/25360dfaa201/41467_2024_50460_Fig1_HTML.jpg

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