Nickel catalyzed chain walking cross-ele ctrophile coupling of alkyl and aryl halides and olefin hydroarylation enabled by electrochemical reduction.
AuthorsGadde, Sathish Kumar
KAUST DepartmentKAUST Catalysis Center (KCC)
King Abdullah University of Science and Technology, Catalysis Center, SAUDI ARABIA.
Physical Science and Engineering (PSE) Division
Online Publication Date2020-03-05
Print Publication Date2020-04-16
Permanent link to this recordhttp://hdl.handle.net/10754/661475
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AbstractThe first electrochemical approach for the nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to afford 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivities under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale proving the potential for the industrial application. Mechanistic investigations suggested the formation of a nickel hydride in the electroreductive chain walking arylation which led to the additional development of a new nickel catalyzed hydroarylation of styrenes providing a series of 1,1-diaryl alkanes in good yields under mild reaction conditions.
CitationGadde, S. K., Peshkov, A., Brzozowska, A., Nikolaienko, P., Zhu, C., & Rueping, M. (2020). Nickel catalyzed chain walking cross-ele ctrophile coupling of alkyl and aryl halides and olefin hydroarylation enabled by electrochemical reduction. Angewandte Chemie International Edition. doi:10.1002/anie.201915418
SponsorsG.S.K., A.P., A.B., P.N.,C.Z and MR acknowledges King Abdullah University of Science and Technology (KAUST) for support and C.Z.acknowledges the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.