Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Adv Synth Catal

Department of Chemistry, Department of Medicinal Chemistry and the Institute for Therapeutics Discovery and Development, University of Minnesota, Twin Cities, 717 Delaware St SE, Minneapolis, Minnesota, USA.

Published: April 2014

A green and mild protocol for the dehydrogenative olefination of cyclic enaminones was devised via palladium catalysis at room temperature using oxygen as the terminal oxidant. The synthetic utility of the olefinated cyclic enaminones afforded a series of unique 1,3,5-trisubstituted benzenes via an unanticipated Diels-Alder tandem reaction. The broad substrate scope and good yields achieved with this new protocol provide an alternative pathway for arene functionalization.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4111264PMC
http://dx.doi.org/10.1002/adsc.201300904DOI Listing

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