Cu‐Catalyzed Phenol O‐Methylation with Methylboronic Acid

A Cu‐catalyzed oxidative cross‐coupling of phenols with methylboronic acid to form aryl methyl ethers has been developed, expanding the scope of Chan‐Evans‐Lam alkylation. Electron‐deficient phenol derivatives with a broad array of functional groups are methylated in high yields. Increased reaction...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-11, Vol.2021 (41), p.5661-5664
Main Authors: Bartlett, Mairead E., Zhu, Yingchuan, Gaffney, Uma Bhagwat, Lee, Joyce, Wu, Miranda, Sharew, Betemariam, Chavez, Angela K., Gorin, David J.
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Copper
Cross coupling
Cross-coupling reactions
Ethers
Functional groups
Methylation
Phenols
Substrates
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Summary:A Cu‐catalyzed oxidative cross‐coupling of phenols with methylboronic acid to form aryl methyl ethers has been developed, expanding the scope of Chan‐Evans‐Lam alkylation. Electron‐deficient phenol derivatives with a broad array of functional groups are methylated in high yields. Increased reaction temperature and catalyst loading enables the methylation of substrates incorporating pyridine and dihydroquinolone motifs. Electron‐rich phenol derivatives are poor substrates for the methylation; the characterization of C−H homodimerization products formed from these substrates illuminates a competing mechanistic pathway. The Cu‐catalyzed oxidative cross‐coupling of phenols with methylboronic acid provides a synthetic route to aryl methyl ethers, expanding the scope of Chan‐Evans‐Lam alkylation. The reaction proceeds under “open flask” conditions with no additional oxidant. Electron‐deficient phenol derivatives are methylated in high yields, and some N‐heterocycles are tolerated.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100902