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Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions
Yuxuan Ding1, Shihui Luo1, Lifu Ma2
1College of Science , China Agricultural University , No. 2, Yuanmingyuan West Road , Beijing 100193 , China.
Abstract:
A general protocol for the reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles has been achieved under single-electron-transfer conditions using Na/15-crown-5/H2O. Electron is supplied by the electride derived from bench-stable sodium dispersions and recoverable 15-crown-5. H2O provides the proton source and suppresses the reduction of aromatic moieties. Compared with the Na/NH3 electride system generated under traditional Birch conditions, this ammonia-free electride system is more practical and features better reactivity and chemoselectivity for the decyanations of a broad range of aliphatic nitriles.
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