Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

Prakash Basnet, Roshan K. Dhungana, Surendra Thapa, Bijay Shrestha, Shekhar Kc, Jeremiah M. Sears, Ramesh Giri

Research output: Contribution to journalArticle

46 Scopus citations

Abstract

We disclose a [(PhO) 3 P]/NiBr 2 -catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H + workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.

Original languageEnglish (US)
Pages (from-to)7782-7786
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number25
DOIs
StatePublished - Jun 27 2018

All Science Journal Classification (ASJC) codes

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

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