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Issue 4, 2012
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C–H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition

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Abstract

A solvent-free synthesis of α-aminonitriles and β-nitroamines by oxidative cross-dehydrogenative coupling under aerobic condition is reported. A catalytic amount of molybdenum(VI) acetylacetonoate was found to catalyze cyanation of tertiary amines to form α-aminonitriles, whereas vanadium pentoxide was found to promote aza-Henry reaction to furnish β-nitroamines. Both of these environmentally benign reactions are performed in the absence of solvents using molecular oxygen as an oxidant.

Graphical abstract: C–H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition

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Submitted
26 Aug 2011
Accepted
12 Oct 2011
First published
13 Oct 2011

Org. Biomol. Chem., 2012,10, 835-842
Article type
Paper

C–H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition

K. Alagiri and K. R. Prabhu, Org. Biomol. Chem., 2012, 10, 835
DOI: 10.1039/C1OB06466E

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