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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Capricious selectivity in electrophilic deuteration of methylenedioxy substituted aromatic compounds
Monika Pohjoispää1, Raúl Mera-Adasme, Dage Sundholm
1Department of Chemistry, University of Helsinki , P.O. Box 55, FIN-00014 Helsinki, Finland.
Abstract:
Ring deuteration via the SEAr mechanism, which is usually problem-free, is found to be troublesome with methylenedioxy substituent aromatics. We report a case where the deuteration not only partially fails at one of the ortho positions but also is completely prevented by a conformation dependent effect at the other o-position. Such selectivity discrepancies are important due to the widespread occurrence of methylenedioxy substituted natural products. Density functional theory calculations were used to elucidate the exchange reaction mechanism in 1,2-dialkoxybenzenes.
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