Increasing rates and scope of reactions: sluggish amines in microwave-heated aminocarbonylation reactions under air.

J Org Chem

Department of Organic Pharmaceutical Chemistry, Uppsala University, Biomedical Centre, Box-574, SE-751 23 Uppsala, Sweden.

Published: July 2003

Commercially available molybdenum hexacarbonyl serves as a convenient and solid carbon monoxide source in palladium-catalyzed aminocarbonylations of aryl bromides and iodides. This improved microwave protocol, relying on DBU as base and THF as solvent, enables rapid couplings using otherwise sluggish anilines, tert-butylamine, and free amino acids. In addition, Cr(CO)(6) and W(CO)(6) were found to be useful alternative CO-releasing reagents. Altogether, 16 different aromatic amides were synthesized under air in 35-95% yield after only 15 min of controlled microwave irradiation.

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http://dx.doi.org/10.1021/jo034382dDOI Listing

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