Silver-Catalyzed Synthesis of Benzyl Ethers via Alkoxylation of Benzylic C(sp3)-H Bonds

Alkoxylation of benzylic C(sp(3))-H bonds has become one of the most important tools for the construction of benzyl ethers from feedstock chemicals. Herein, we reported a silver catalyzed alkoxylation of benzylic C(sp(3))-H bonds employing potassium persulfate as an oxidant at room temperature. This strategy showed good functional-group tolerance, site selectivity, and chemoselectivity. The reaction proceeded smoothly in the presence of various primary, secondary, and tertiary alcohol nucleophiles, affording corresponding benzyl ethers. Combined experimental studies provided mechanistic insights into the possible radical pathways. Furthermore, a possible mechanism was proposed for this method.

Automated summary

In this study, a silver catalyzed alkoxylation of benzylic C(sp(3))-H bonds using potassium persulfate as an oxidant at room temperature was reported. This strategy exhibited good functional-group tolerance, site selectivity, and chemoselectivity, allowing the synthesis of corresponding benzyl ethers in the presence of various primary, secondary, and tertiary alcohol nucleophiles. Mechanistic insights into the possible radical pathways were obtained through experimental studies, and a possible mechanism for this method was proposed.