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通过可见光诱导的配体到金属电荷转移,Lewis酸性离子液体催化的α-烷基-α-甲基丙烯酰基苯甲酰胺与烷烃的自由基级联烷基化/环化反应:合成烷基化异喹啉-1,3(2,4)-二酮

Lewis Acidic Ionic-Liquid-Catalyzed Radical-Cascade Alkylation/Cyclization of -Alkyl--methacryloyl Benzamides with Alkanes via Visible-Light-Induced Ligand-to-Metal Charge Transfer: Access to Alkylated Isoquinoline-1,3(2,4)-diones.

作者信息

Zhang Tao, Ren Xinxin, Li Jingkun, Wang Yanhong, Wang Bin, Chen Ziren, Xia Yu, Wu Shaofeng, Liu Chenjiang, Zhang Yonghong

机构信息

Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, People's Republic of China.

出版信息

Org Lett. 2024 Dec 6;26(48):10259-10266. doi: 10.1021/acs.orglett.4c03697. Epub 2024 Nov 21.

Abstract

With the flourishing progress of ligand-to-metal charge transfer (LMCT) photocatalysis, various metals were developed as catalysts to activate abundant alkane feedstocks for the synthesis of functionalized organic compounds. However, to the best of our knowledge, most of the LMCT catalysts are difficult to recover and reuse for the next cycles. Herein, we report a reusable Lewis acidic ionic liquid (LAIL)-catalyzed radical-cascade alkylation/cyclization of -alkyl--methacryloyl benzamides with unactivated alkanes for the synthesis of alkylated isoquinoline-1,3-(2,4)-diketones. The protocol features mild reaction conditions, high atom utilization efficiency, scale-up synthesis, simple operation, and recycling of catalysts.

摘要

随着配体到金属电荷转移(LMCT)光催化的蓬勃发展,各种金属被开发用作催化剂,以活化丰富的烷烃原料来合成功能化有机化合物。然而,据我们所知,大多数LMCT催化剂难以回收并用于下一轮循环。在此,我们报道了一种可重复使用的路易斯酸性离子液体(LAIL)催化的α-烷基-β-甲基丙烯酰基苯甲酰胺与未活化烷烃的自由基串联烷基化/环化反应,用于合成烷基化异喹啉-1,3-(2,4)-二酮。该方法具有反应条件温和、原子利用率高、可放大合成、操作简单以及催化剂可循环利用等特点。

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