Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

Vivek Aryal, Lucas J. Chesley, Doleshwar Niroula, Rishi R. Sapkota, Roshan K. Dhungana, Ramesh Giri

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7 Scopus citations

Abstract

We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp3)-branched δ-arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.

Original languageEnglish (US)
Pages (from-to)7262-7268
Number of pages7
JournalACS Catalysis
Volume12
Issue number12
DOIs
StatePublished - Jun 17 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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