Check out our recent work on unstrained C–C activation!
We report a site-selective C-demethylation of phenols and anilines enabled by a removable mono-directing group.
Congrats to Yibin, Liyan, Linda, and Congjun @congjunyu.bsky.social !
pubs.acs.org/doi/full/10....
The activation of unstrained nonpolar C–C bonds, such as C(aryl)–C(alkyl) bonds, remains challenging to achieve. Existing catalytic strategies predominantly rely on bidentate chelating directing groups (DGs) or special substrates. Herein, we report a Ru-catalyzed activation of C(aryl)–C(methyl) bonds enabled by a removable mono-DG. By employing a bulky phosphinite or aminophosphine-DG that can be easily installed and removed later, a methyl group at the ortho position of phenols and anilines can be smoothly deleted under the hydrogenolysis condition. This reaction exhibits a broad substrate scope and excellent functional group tolerance. Mechanistic studies suggest that a Ru–hydride species generated in situ is responsible for the C(aryl)–C(methyl) bond activation, with methane identified as a byproduct.
