Cu-Catalyzed Phenol O-Methylation with Methylboronic Acid

Authors

Mairead E. Bartlett, Smith College
Yingchuan Zhu, Smith College
Uma Bhagwat Gaffney, Smith College
Joyce Lee, Smith College
Miranda Wu, Smith College
Betemariam Sharew, Smith College
Angela K. Chavez, Smith College
David J. Gorin, Smith CollegeFollow

Document Type

Article

Publication Date

11-8-2021

Publication Title

European Journal of Organic Chemistry

Abstract

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.

Keywords

Alkylation, Catalysis, Copper, Cross-coupling reactions, Methylation

Volume

2021

Issue

41

First Page

5661

Last Page

5664

DOI

10.1002/ejoc.202100902

ISSN

1434193X

Rights

© 2021 Wiley-VCH GmbH

Comments

Archived as published. Open access article.

Recommended Citation

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.
https://scholarworks.smith.edu/chm_facpubs/62