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Scientific article
English

Highly Enantiomerically Enriched Planar Chiral Naphtalene Tricarbonylchromium Complexes

Published inChemistry - an Asian journal, vol. 1, no. 3, p. 459-468
Publication date2006
Abstract

Lithiation/electrophile trapping reactions were carried out with the highly enantiomerically enriched complex [Cr(5-bromonaphthalene)(CO)3]. Electrophile quenching with ClPPh2, PhCHO, and (Me3SiO)2 afforded the enantiomerically enriched (>97% ee) planar chiral 5-substituted naphthalene complexes with PPh2, CH(Ph)OH, and OH substituents, respectively. Very mild Pd-catalyzed Suzuki-Miyaura cross-coupling reactions were developed and applied to the highly labile [Cr(5-bromonaphthalene)(CO)3] to give nine new planar chiral aryl-, heteroaryl-, alkynyl-, and alkenylnaphthalene chromium complexes with high enantiomeric purity. The efficient ambient-temperature coupling reactions with borinates prepared in situ were also applied to a number of chlorobenzene complexes and to aryl and vinyl halides.

Keywords
  • Chiral complexes
  • Chromium
  • Cross-coupling
  • Enantioselectivity
  • Naphthalene
Citation (ISO format)
CUMMING, Graham, BERNARDINELLI, Gérald Hugues, KUNDIG, Ernst Peter. Highly Enantiomerically Enriched Planar Chiral Naphtalene Tricarbonylchromium Complexes. In: Chemistry - an Asian journal, 2006, vol. 1, n° 3, p. 459–468. doi: 10.1002/asia.200600106
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ISSN of the journal1861-471X
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