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Scientific article
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English

Asymmetric Pd-NHC*-catalyzed coupling reactions

Published inPure and applied chemistry, vol. 84, no. 8, p. 1741-1748
Publication date2012
Abstract

Very high asymmetric inductions result in the Pd-catalyzed intramolecular arylation of amides to give 3,3-disubstituted oxindoles when new in situ-generated chiral N‑heterocyclic carbene (NHC*) ligands are employed. Structural studies show that conformational locking to minimize allylic strain is the key to understanding the function of these ligands. New applications of these ligands in the frontier area of asymmetric coupling reactions involving C(sp3)–H bonds are detailed. Highly enantioenriched fused indolines are accessible using either preformed- or in situ-generated Pd-NHC* catalysts. Remarkably, this occurs at high temperature (140–160 °C) via excellent asymmetric recognition of an enantiotopic C–H bond in an unactivated methylene unit.

Keywords
  • Asymmetry
  • C–H bond reactivity
  • Coupling reactions
  • N-heterocyclic carbenes
  • Palladium
Citation (ISO format)
KUNDIG, Ernst Peter et al. Asymmetric Pd-NHC*-catalyzed coupling reactions. In: Pure and applied chemistry, 2012, vol. 84, n° 8, p. 1741–1748. doi: 10.1351/PAC-CON-12-02-10
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Article (Published version)
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ISSN of the journal0033-4545
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