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通过共振声学混合实现的快速且可扩展的钌催化间位C-H烷基化反应。

Rapid and scalable ruthenium catalyzed meta-C-H alkylation enabled by resonant acoustic mixing.

作者信息

Dey Arnab, Kancherla Rajesh, Pal Kuntal, Kloszewski Nathan, Rueping Magnus

机构信息

KAUST Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.

出版信息

Commun Chem. 2024 Dec 18;7(1):295. doi: 10.1038/s42004-024-01390-1.

DOI:10.1038/s42004-024-01390-1
PMID:39695309
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11655853/
Abstract

Synthetic chemistry approaches for direct C-H bond alkylation offers a promising alternative to traditional functional-group-centered strategies which often involve multi-step procedures and may suffer from a variety of challenges including scalability. Here, we introduce resonant mixing as an efficient method for meta-C-H alkylation of arenes using a Ru-catalyst, avoiding the need for bulk solvents, external temperature, or light. The described methodology is highly rapid, enabling multigram-scale synthesis of meta-alkylation products within a short reaction time and achieving a very high turnover frequency. The reaction operates via a radical mechanism and is characterized by its mild reaction conditions, substrate compatibility, and exceptional meta-selectivity, all while significantly reducing reaction times.

摘要

用于直接C-H键烷基化的合成化学方法为传统的以官能团为中心的策略提供了一种有前景的替代方案,传统策略通常涉及多步程序,并且可能面临包括可扩展性在内的各种挑战。在此,我们介绍共振混合作为一种使用钌催化剂对芳烃进行间位C-H烷基化的有效方法,无需大量溶剂、外部加热或光照。所描述的方法速度极快,能够在短反应时间内实现多克规模的间位烷基化产物合成,并达到非常高的周转频率。该反应通过自由基机理进行,其特点是反应条件温和、底物兼容性好以及具有出色的间位选择性,同时显著缩短了反应时间。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/b5cc787833f4/42004_2024_1390_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/7967d6c51420/42004_2024_1390_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/9788a2b91790/42004_2024_1390_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/63568a9d9402/42004_2024_1390_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/2a882452f73f/42004_2024_1390_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/b5cc787833f4/42004_2024_1390_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/7967d6c51420/42004_2024_1390_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/9788a2b91790/42004_2024_1390_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/63568a9d9402/42004_2024_1390_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/2a882452f73f/42004_2024_1390_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/13e4/11655853/b5cc787833f4/42004_2024_1390_Fig5_HTML.jpg

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