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Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis

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Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.

OriginalsprogEngelsk
Artikelnummere202112390
TidsskriftAngewandte Chemie - International Edition
Vol/bind61
Nummer4
Antal sider9
ISSN1433-7851
DOI
StatusUdgivet - 21 jan. 2022

Bibliografisk note

Funding Information:
We are highly appreciative of financial support from the Danish National Research Foundation (grant no. DNRF118), the Independent Research Fund Denmark—Technology and Production (grant no. 4148‐00031), and Aarhus University for financial support.

Publisher Copyright:
© 2021 Wiley-VCH GmbH

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