Regioselective oxidative cleavage of conjugated dienes to access ,-unsaturated nitriles

A highly regioselective oxidative cleavage method has been developed for the synthesis of alpha,beta-unsaturated nitriles from unsymmetric conjugated dienes. This transformation selectively cleaved the terminal C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C double bond, providing moderate to good yields of the desired alpha,beta-unsaturated nitriles. Notably, electron-deficient dienes exhibited superior regioselectivity over electron-rich ones. This versatile method displayed a broad substrate scope and excellent tolerance towards various functional groups. Additionally, the synthesis of N-15 atom labeled alpha,beta-unsaturated nitriles from N-15 isotopically labeled ammonium chloride was achieved. This isotopically labeled compound is valuable for the synthesis of N-15 atom labeled rilpivirine, a well-known anti-HIV pharmaceutical. A highly regioselective oxidative cleavage method has been developed for the synthesis of alpha,beta-unsaturated nitriles and N-15 atom labeled alpha,beta-unsaturated nitriles from unsymmetric conjugated dienes and ammonium salts.