Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles

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

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93 Scopus citations

Abstract

We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products.

Original languageEnglish (US)
Pages (from-to)10653-10656
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number31
DOIs
StatePublished - Aug 9 2017

All Science Journal Classification (ASJC) codes

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

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