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

Angewandte Chemie
Stig D FriisStephen L Buchwald

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.

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Citations

May 22, 2018·Chemical Communications : Chem Comm·Liqun JinXinquan Hu
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Dec 6, 2018·Angewandte Chemie·Guoqiang WangShuhua Li
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Nov 3, 2021·Angewandte Chemie·Anne K RavnTroels Skrydstrup

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