Palladium-Catalyzed Divergent Cyclopropanation by Regioselective Solvent-Driven C(sp3)−H Bond Activation

Da Sol Chung, Jae Sung Lee, Ho Ryu, Jiyong Park, Hyunjoong Kim, Joo Hyun Lee, U. Bin Kim, Won Koo Lee, Mu Hyun Baik, Sang gi Lee

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16 Scopus citations

Abstract

Reported is a tandem palladium-catalyzed Heck/regioselective C(sp3)−H activation reaction for the divergent synthesis of spiro- and fused-cyclopropanated indolines from N-methallylated 2-bromoarylamides. The regioselectivity of the C−H bond activation in the σ-alkylPdII intermediate is controlled by the solvent used. DFT calculations suggest that the polarity of solvent molecules could influence the transition-state energy, leading to a bifurcation of the C−H bond activation in the σ-alkylPdII intermediate.

Original languageEnglish
Pages (from-to)15460-15464
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number47
DOIs
StatePublished - 19 Nov 2018

Keywords

  • C−H activation
  • heterocylces
  • palladium
  • reaction mechanisms
  • solvent effects

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