A dual palladium and copper hydride catalyzed approach for alkyl-aryl cross-coupling of aryl halides and olefins
Author(s)
Friis, Stig During; Pirnot, Michael T; Dupuis, Lauren N.; Buchwald, Stephen Leffler
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We report an efficient means of sp2-sp3 cross coupling for a variety of terminal monosubstituted olefins with aryl electrophiles using Pd and CuH catalysis. In addition to its applicability to a range of aryl bromide substrates, this process was also suitable for electron-deficient aryl chlorides, furnishing higher yields than the corresponding aryl bromides in these cases. The optimized protocol does not require the use of a glovebox and employs air-stable Cu and Pd complexes as precatalysts. A reaction on 10 mmol scale further highlighted the practical utility of this protocol. Employing a similar protocol, a series of cyclic alkenes were also examined. Cyclopentene was shown to undergo efficient coupling under these conditions. Lastly, deuterium-labeling studies indicate that deuterium scrambling does not take place in this sp2-sp3 cross coupling, implying that β-hydride elimination is not a significant process in this transformation.
Date issued
2017-06Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Angewandte Chemie International Edition
Publisher
Wiley
Citation
Friis, Stig D., et al., "A dual palladium and copper hydride catalyzed approach for alkyl-aryl cross-coupling of aryl halides and olefins." Angewandte Chemie International Edition 56, 25 (June 2017): p. 7242-46 doi 10.1002/ANIE.201703400 ©2017 Author(s)
Version: Author's final manuscript
ISSN
0570-0833