Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination

Roshan K. Dhungana, Vivek Aryal, Doleshwar Niroula, Rishi R. Sapkota, Margaret G. Lakomy, Ramesh Giri

Research output: Contribution to journalArticlepeer-review

Abstract

We disclose a nickel-catalyzed reaction, which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with NiBr2⋅DME as a catalyst and LiOtBu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron-rich and electron-deficient arylboronate esters. The reaction also worked with both cyclic and acyclic alkenyl triflates. Control experiments indicate that carbonyl coordination is required for the reaction to proceed.

Original languageEnglish (US)
Pages (from-to)19092-19096
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number35
DOIs
StatePublished - Aug 23 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination'. Together they form a unique fingerprint.

Cite this