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A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.


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 ?-hydride elimination is not a significant process in this transformation.

SUBMITTER: Friis SD 

PROVIDER: S-EPMC5572809 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Friis Stig D SD   Pirnot Michael T MT   Dupuis Lauren N LN   Buchwald Stephen L SL  

Angewandte Chemie (International ed. in English) 20170516 25


We report an efficient means of sp<sup>2</sup> -sp<sup>3</sup> 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 compl  ...[more]

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