Photoinduced Etherification of Less-Strained Cycloketoxime Esters Enabled by C-C Bond Cleavage

We report a general, scalable, and convenient photochemical process for diversities of distal oxygenated nitriles from corresponding less-strained ketoxime esters allowing one-step introductions of ether and cyano groups, which avoids the utilization of toxic cyanide reagents. A wide range of ketoxime esters involving five-membered to eight-membered cycloketoxime esters and linear ketoxime esters participate smoothly under operately simple and mild conditions, affording structurally variable ring-opening products.

Automated summary

A general, scalable, and convenient photochemical process is reported for the synthesis of various distal oxygenated nitriles from less-strained ketoxime esters. This method allows for one-step introductions of ether and cyano groups, eliminating the need for toxic cyanide reagents. The reaction is applicable to a wide range of cycloketoxime esters and linear ketoxime esters, providing structurally diverse ring-opening products under simple and mild conditions.