A highly regioselective oxidative cleavage method has been developed for the synthesis of α,β-unsaturated nitriles from unsymmetric conjugated dienes. This transformation selectively cleaved the terminal CC double bond, providing moderate to good yields of the desired α,β-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 α,β-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.

中文翻译：

---

共轭二烯的区域选择性氧化裂解得到α,β-不饱和腈

开发了一种高度区域选择性的氧化裂解方法，用于从不对称共轭二烯合成α,β-不饱和腈。这种转化选择性地裂解了末端 C C 双键，从而提供了所需 α,β-不饱和腈的中等至良好产率。值得注意的是，缺电子二烯比富电子二烯表现出优异的区域选择性。这种多功能方法显示出广泛的底物范围和对各种官能团的优异耐受性。此外，还实现了由N-15同位素标记的氯化铵合成N-15原子标记的α,β-不饱和腈。这种同位素标记的化合物对于合成 N-15 原子标记的利匹韦林（一种著名的抗 HIV 药物）很有价值。