Nickel-catalyzed para-selective carboxylation of phenols with CBr4/MeOH

1,10-Phenanthroline-assisted, Ni(ii)-catalyzed para-carboxylation of phenol derivatives is reported. A wide variety of substituted phenols are compatible with this reaction and led to para-carboxylated products in moderate to good yields. Impressively, various bioactive compounds are selectively car...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-07, Vol.9 (14), p.3876-3881
Main Authors: Tu, Guangliang, Ju, Guodong, Huang, Zhibin, Shun-Jun Ji, Zhao, Yingsheng
Format: Article
Language:English
Subjects:
Benzene
Bioactive compounds
Biological activity
Carboxylation
Catalysts
Hydroxyl groups
Nickel
Organic chemistry
Phenols
Selectivity
Steric hindrance
Syringate
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Summary:1,10-Phenanthroline-assisted, Ni(ii)-catalyzed para-carboxylation of phenol derivatives is reported. A wide variety of substituted phenols are compatible with this reaction and led to para-carboxylated products in moderate to good yields. Impressively, various bioactive compounds are selectively carboxylated, and several bioactive molecules, including methyl syringate, methyl gallate, and dimethyl gallate, could also be directly carboxylated in one step. Mechanistic studies show that the coordination of Ni(ii) with the hydroxyl group of phenol enhances the activity of hydroxyl group-bound benzene ring, leading to high para-selectivity, as influenced by the nickel catalyst and ligand steric hindrance.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00462c