Iron-catalysed oxidative amidation of alcohols with amines

20 04 2013

ORGANIC CHEMISTRY SELECT

Iron-catalysed oxidative amidation of alcohols with amines

Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB40170G, Paper
Silvia Gaspa, Andrea Porcheddu, Lidia De Luca
Dipartimento di Chimica e Farmacia, Università degli Studi di Sassari, Sassari, Italy
A new iron-catalysed oxidative amidation of differently substituted benzylic alcohols with mono- and di-substituted amines was developed.

General procedures for amides 4a-q:

An amine (0.32 mmol) was added to a solution of N-chlorosuccinimide (0.352 mmol) in 10 mL of acetonitrile under N2 atmosphere and at room temperature. The reaction was monitored by TLC until disappearance of the
amine (1-2 hours), then were added an alcohol (1.6 mmol), TBHP (1.6 mmol, 0.22 mL of a 70 wt% in water) and FeCl3.6H2O (0.045 mmol) under N2 atmosphere.The resulting reaction mixture was heated in an oil bath at 85°C (the reaction was monitored by TLC until disappearance of Nchloroamine). Then the reaction mixture was quenched with 20…

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