Iron-catalysed oxidative amidation of alcohols with amines

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

http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/C3OB40170G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FOB+%28RSC+-+Org.+Biomol.+Chem.+latest+articles%29

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 mL of a saturated solution of Na2SO3 (for removal of excess TBHP)
and extracted three times with 40 mL of diethyl ether. The combined organic phases were dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to provide the desired amides 4a-q

check out supplementary info from this article provides experimental  procedure, spectroscopy data