Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts

Basnet, Prakash; KC, Shekhar; Dhungana, Roshan K.; Shrestha, Bijay; Boyle, Timothy J.; Giri, Ramesh

doi:10.1021/jacs.8b09401

Title: Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts

Journal Article · Mon Nov 05 00:00:00 EST 2018 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.8b09401· OSTI ID:1485460

Basnet, Prakash ^[1]; KC, Shekhar ^[1]; Dhungana, Roshan K. ^[1]; Shrestha, Bijay ^[1];

^[2];

^[1]

The Univ. of New Mexico, Albuquerque, NM (United States)
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Here, we disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective γ,δ-diarylation of unactivated alkenes in simple ketimines with aryl halides and arylzinc reagents. The bimetallic synergy, which generates cationic Ni(II) species during reaction, promotes migratory insertion and transmetalation steps and suppresses β-H elimination and cross-coupling, the major side reactions that cause serious problems during alkene difunctionalization. This diarylation reaction proceeds at remote locations to imines to afford, after simple H⁺ workup, diversely substituted γ,δ-diaryl ketones that are otherwise difficult to access readily with existing methods.

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Research Organization:: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1485460

Report Number(s):: SAND-2018-12087J; 668982

Journal Information:: Journal of the American Chemical Society, Vol. 140, Issue 46; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 86 works

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