Reductive monoalkylation of aromatic and aliphatic nitro compounds and the corresponding amines with nitriles.
[reaction: see text] A simple, selective, rapid, and efficient procedure for the synthesis of secondary amines from the reductive alkylation of either aliphatic or aromatic nitro compounds and the corresponding amines is reported. Ammonium formate is used as the hydrogen source and Pd/C as the hydrogen transfer catalyst. The reaction is carried out at room temperature. The rate differences for the preferential formation of secondary over tertiary products are due to both steric and electronic factors.
Nacario
Ruel
R
Department of Medicinal and Biological Chemistry, College of Pharmacy, University of Toledo, Toledo, OH 43606, USA.
Kotakonda
Shailaja
S
Fouchard
David M D
DM
Tillekeratne
L M Viranga
LM
Hudson
Richard A
RA
D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis*; D005561:Formates; D006859:Hydrogen / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D000588:Amines; D005561:Formates; D009570:Nitriles; D009574:Nitro Compounds; C030544:formic acid; D006859:Hydrogen