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电化学连续流芳香 C-H 羟化。

Electrochemical aromatic C-H hydroxylation in continuous flow.

机构信息

State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, 361005, Xiamen, China.

Key Laboratory of Chemical Biology of Fujian Province, Xiamen University, 361005, Xiamen, China.

出版信息

Nat Commun. 2022 Jul 8;13(1):3945. doi: 10.1038/s41467-022-31634-4.

DOI:10.1038/s41467-022-31634-4
PMID:35803941
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9270493/
Abstract

The direct hydroxylation of arene C-H bonds is a highly sought-after transformation but remains an unsolved challenge due to the difficulty in efficient and regioselective C-H oxygenation and high reactivity of the phenolic products leading to overoxidation. Herein we report electrochemical C-H hydroxylation of arenes in continuous flow for the synthesis of phenols. The method is characterized by broad scope (compatible with arenes of diverse electronic properties), mild conditions without any catalysts or chemical oxidants, and excellent scalability as demonstrated by the continuous production of 1 mol (204 grams) of one of the phenol products.

摘要

芳环 C-H 键的直接羟化是一种备受关注的转化反应,但由于高效和区域选择性 C-H 氧化以及酚类产物的高反应性导致过度氧化,该反应仍然是一个未解决的挑战。在此,我们报告了在连续流中通过电化学 C-H 羟化芳环来合成酚类化合物的方法。该方法具有广泛的适用范围(可兼容具有不同电子性质的芳环)、温和的条件(无需使用任何催化剂或化学氧化剂),以及出色的可扩展性,如通过连续生产 1 摩尔(204 克)一种酚类产物得到证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/bce3b6e5c4d3/41467_2022_31634_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/419ab49dd019/41467_2022_31634_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/36a59b3f7224/41467_2022_31634_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/af32330da3ed/41467_2022_31634_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/f72cf26c16a5/41467_2022_31634_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/bce3b6e5c4d3/41467_2022_31634_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/419ab49dd019/41467_2022_31634_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/36a59b3f7224/41467_2022_31634_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/af32330da3ed/41467_2022_31634_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/f72cf26c16a5/41467_2022_31634_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ead2/9270493/bce3b6e5c4d3/41467_2022_31634_Fig5_HTML.jpg

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