Oxidant-free conversion of primary amines to nitriles

KNT Tseng, AM Rizzi, NK Szymczak

Index: Tseng, Kuei-Nin T.; Rizzi, Andrew M.; Szymczak, Nathaniel K. Journal of the American Chemical Society, 2013 , vol. 135, # 44 p. 16352 - 16355

Full Text: HTML

Citation Number: 40

Abstract

An amide-derived NNN-Ru (II) hydride complex catalyzes oxidant-free, acceptorless, and chemoselective dehydrogenation of primary and secondary amines to the corresponding nitriles and imines with liberation of dihydrogen. The catalyst system tolerates oxidizable functionality and is selective for the dehydrogenation of primary amines (− CH2NH2) in the presence of amines without α-CH hydrogens.

~48%

~25%

~53%

~65%

Synthesis of 7-cyano-and 7-acetamido-indoles via cyanocarbon...

[Kolis, Stanley P.; Clayton, Marcella T.; Grutsch, John L.; Faul, Margaret M. Tetrahedron Letters, 2003 , vol. 44, # 30 p. 5707 - 5710]

A practical method for the preparation of nitriles from prim...

[Bose, D. Subhas; Jayalakshmi, B. Synthesis, 1999 , # 1 p. 64 - 65]

PALLADIUM CATALYZED REACTION OF ARYL BROMIDES WITH CYANOMETH...

[Kosugi, Masanori; Ishiguro, Masahiro; Negishi, Yoshikazu; Sano, Hiroshi; Migita, Toshihiko Chemistry Letters, 1984 , p. 1511 - 1512]

Reactions of 4-chloro-1-nitrobenzene with o-substituted phen...

[Vejdelek, Zdenek; Holubek, Jiri; Ryska, Miroslav; Koruna, Ivan; Svatek, Emil; et.al. Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 10 p. 2545 - 2563]

Facile synthesis of nitriles from primary nitro compounds vi...

[Tetrahedron Letters, , vol. 37, # 43 p. 7791 - 7794]