Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation

RL Patman, VM Williams, JF Bower, MJ Krische

Research output: Contribution to journalArticle (Academic Journal)peer-review

77 Citations (Scopus)

Abstract

Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.
Translated title of the contributionCarbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation
Original languageEnglish
Pages (from-to)5220-5223
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number28
DOIs
Publication statusPublished - 2008

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