A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

S Diez-Gonzalez, H Kaur, FK Zinn, ED Stevens, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

167 Citations (Scopus)

Abstract

The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

Original languageEnglish
Pages (from-to)4784-4796
Number of pages13
JournalThe Journal of Organic Chemistry
Volume70
Issue number12
DOIs
Publication statusPublished - 10 Jun 2005

Keywords

  • HETEROCYCLIC CARBENE COMPLEXES
  • ASYMMETRIC HYDROSILYLATION
  • ENANTIOSELECTIVE HYDROSILYLATION
  • CARBONYL-COMPOUNDS
  • ALPHA,BETA-UNSATURATED KETONES
  • HETEROAROMATIC KETONES
  • CONJUGATE REDUCTION
  • STABLE CARBENES
  • DIALKYL KETONES
  • ARYL KETONES

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