A dual palladium and copper hydride catalyzed approach for alkyl-aryl cross-coupling of aryl halides and olefins
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nihms894221.pdf
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Author(s)
Friis, Stig During
Pirnot, Michael T
Dupuis, Lauren N.
Buchwald, Stephen Leffler
Date Issued
June 2017
Journal
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
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1002/ANIE.201703400
