Electron transfer reduction of nitriles using SmI2-Et3N-H2O: synthetic utility and mechanism.
The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm(II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile precursors.
School of Chemistry, University of Manchester , Oxford Road, Manchester, M13 9PL, U.K.
Michal
M
Szostak
Brice
B
Sautier
Malcolm
M
Spain
David J
DJ
Procter
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004579:Electron Transport; D007454:Iodides / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry; D008672:Metals, Alkali / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*; D014867:Water
D000588:Amines; D007454:Iodides; D058115:Lewis Bases; D008672:Metals, Alkali; D009570:Nitriles; D014867:Water; D012493:Samarium; C409809:samarium diiodide