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A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl–Aryl Cross‐Coupling of Aryl Halides and Olefins
Author(s) -
Friis Stig D.,
Pirnot Michael T.,
Dupuis Lauren N.,
Buchwald Stephen L.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703400
Subject(s) - aryl , chemistry , catalysis , alkyl , palladium , combinatorial chemistry , cyclopentene , bromide , hydride , organic chemistry , medicinal chemistry , hydrogen
Abstract We report an efficient means of sp 2 –sp 3 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 sp 2 ‐sp 3 cross coupling, implying that β‐hydride elimination is not a significant process in this transformation.