Highly Active in Situ Catalysts for Anti-Markovnikov Hydration of Terminal Alkynes

Aurélie Labonne, Thomas Kribber, and Lukas Hintermann*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany
Org. Lett., 2006, 8 (25), pp 5853–5856
DOI: 10.1021/ol062455k
Publication Date (Web): November 16, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, lukas.hintermann@oc.rwth-aachen.de

Abstract

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The anti-Markovnikov hydration of terminal alkynes to give aldehydes is catalyzed by complexes derived in situ from air-stable [CpRu(η6-naphthalene)]PF6 (C) and 6-aryl-2-diphenylphosphinopyridines (L). Ligands L are readily available from a modular synthesis. Increasing the size of the ligand C-6 aryl group in the order R = Ph < mesityl < 2,4,6-triisopropylphenyl < (2,4,6-triphenyl)phenyl gave hydration catalysts of highest known activity.

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History

  • Published In Issue December 07, 2006
  • Received October 5, 2006

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