European Journal of Organic Chemistry
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.
Alkylation, Catalysis, Copper, Cross-coupling reactions, Methylation
© 2021 Wiley-VCH GmbH
Bartlett, Mairead E.; Zhu, Yingchuan; Gaffney, Uma Bhagwat; Lee, Joyce; Wu, Miranda; Sharew, Betemariam; Chavez, Angela K.; and Gorin, David J., "Cu-Catalyzed Phenol O-Methylation with Methylboronic Acid" (2021). Chemistry: Faculty Publications, Smith College, Northampton, MA.
Archived as published. Open access article.