Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals

Kwihwan Kobayashi; Shingo Komatsuzaki; Shun-Ya Onozawa; Koichiro Masuda; Shū Kobayashi

doi:10.1039/d3ob01266b

Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals

Org Biomol Chem. 2023 Oct 25;21(41):8259-8262. doi: 10.1039/d3ob01266b.

Authors

Kwihwan Kobayashi¹, Shingo Komatsuzaki¹, Shun-Ya Onozawa¹, Koichiro Masuda¹, Shū Kobayashi^{1

2}

Affiliations

¹ Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Central 5, Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan. kobayashi-kwihwan@aist.go.jp.
² Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 111-0033, Japan.

PMID: 37695162
DOI: 10.1039/d3ob01266b

Abstract

We report an environmentally friendly, aluminium-catalysed, halide- and transition metal-free method for the synthesis of aryl enol ethers from phenols and dimethyl ketals that involves ketal exchange driven by the removal of methanol. The obtained aryl enol ethers were transformed into the corresponding diaryl ethers by Pd/C-catalysed dehydrogenation or DDQ oxidation.