Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines

…, Y Fujita, T Mizusaki, S Betsuin, H Takamatsu…

Index: Ikawa, Takashi; Fujita, Yuki; Mizusaki, Tomoteru; Betsuin, Sae; Takamatsu, Haruki; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao Organic and Biomolecular Chemistry, 2012 , vol. 10, # 2 p. 293 - 304

Full Text: HTML

Citation Number: 19

Abstract

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytichydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc ...

Related Articles:

Conversion of a (sp 3) C–F bond of alkyl fluorides to (sp 3) C–X (X= Cl, C, H, O, S, Se, Te, N) bonds using organoaluminium reagents

[Terao, Jun; Begum, Shameem Ara; Shinohara, Yoshiaki; Tomita, Masahiro; Naitoh, Yoshitaka; Kambe, Nobuaki Chemical Communications, 2007 , # 8 p. 855 - 857]

Vinyl-copper derivatives XII: Stereospecific synthesis of allylic amines by aminomethylation of organocopper reagents

[Germon, C.; Alexakis, A.; Normant, J. F. Tetrahedron Letters, 1980 , vol. 21, p. 3763 - 3766]

Cytostatica

[Westphal; Jerchel Chemische Berichte, 1940 , vol. 73, p. 1007]

The Hydrogenation of Amides and Ammonium Salts. The Transalkylation of Tertiary Amines

[Schneider et al. Journal of the American Chemical Society, 1952 , vol. 74, p. 4287,4288]

The Hydrogenation of Amides and Ammonium Salts. The Transalkylation of Tertiary Amines

[Schneider et al. Journal of the American Chemical Society, 1952 , vol. 74, p. 4287,4288]

More Articles...