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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23 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

Bibliographical note

Funding Information:
This work was made possible by the support of the National Research Foundation (NRF-2016R1A2B2013727). D.S.C. acknowledges the Solvay Fellowship. We thank Dr. Y. Kim for X-ray analysis. We also thank Prof. S. Chang at KAIST for use of the time-resolved infrared spectrometer. M.-H.B. acknowledges the financial support from the Institute for Basic Science (IBS-R10-D1).

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

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