Reductive Cleavage of Unactivated Carbon–Cyano Bonds under Ammonia-Free Birch Conditions
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. H2...
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Veröffentlicht in: | Journal of organic chemistry 2019-12, Vol.84 (24), p.15827-15833 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b02028 |