A well-defined monomeric aluminum complex as an efficient and general catalyst in the Meerwein-Ponndorf-Verley reduction

Brian McNerney, Bruce Whittlesey, David B. Cordes, Clemens Krempner

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The metal-catalyzed Meerwein-Ponndorf-Verley (MPV) reduction allows for the mild and sustainable reduction of aldehydes and ketones but has not found widespread application in organic synthesis due to the high catalyst loading often required to obtain satisfactory yields of the reduced product. We report here on the synthesis and structure of a sterically extremely overloaded siloxide-supported aluminum isopropoxide capable of catalytically reducing a wide range of aldehydes and ketones (52 examples) in excellent yields under mild conditions and with low catalyst loadings. The unseen activity of the developed catalyst system in MPV reductions is due to its unique monomeric nature and the neutral donor isopropanol weakly coordinating to the aluminum center. The present work implies that monomeric aluminum alkoxide catalysts may be attractive alternatives to transition-metalbased systems for the selective reduction of aldehydes and ketones to primary and secondary alcohols.

Original languageEnglish
Pages (from-to)14959-14964
Number of pages6
JournalChemistry - A European Journal
Volume20
Issue number46
DOIs
StatePublished - Nov 10 2014

Keywords

  • Aldehydes
  • Aluminum
  • Ketones
  • MPV reduction
  • Siloxide

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