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

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

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)15586-15590
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number46
DOIs
StatePublished - Nov 21 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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