Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes

Ciril Jimeno, Sonia Sayalero, Torstein Fjermestad, Gisela Colet, Feliu Maseras, Miquel A. Pericàs

Research output: Contribution to journalArticleResearchpeer-review

69 Citations (Scopus)

Abstract

(Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Original languageEnglish
Pages (from-to)1098-1101
JournalAngewandte Chemie - International Edition
Volume47
Issue number6
DOIs
Publication statusPublished - 11 Feb 2008

Keywords

  • Asymmetric catalysis
  • Boron
  • Density functional calculations
  • Reaction mechanisms
  • Zinc

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