Prev. Article Next Article Table of Contents

Note

Me₂Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones

Supporting Info

Pier Giorgio Cozzi,*^† Jens Rudolph,^‡^§ Carsten Bolm,^‡ Per-Ola Norrby, and Claudia Tomasini^†

Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Universit di Bologna, Via Selmi 2, 40126 Bologna, Italy, Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056, Aachen, Germany, and Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark piergiorgio.cozzi@unibo.it

J. Org. Chem., 2005, 70 (14), pp 5733–5736

DOI: 10.1021/jo050115r

Publication Date (Web): June 7, 2005

To whom correspondence should be addressed. Fax: +39 0512099456.

†

Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum, Università di Bologna.

‡

RWTH Aachen University.

New address: BASF AG, GCB/O - M313, 67056 Ludwigshafen, Germany.

Technical University of Denmark.

Abstract

Contrary to expectations, commercially available 2 M Me₂Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave “ligand like”. Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue July 08, 2005
Received January 20, 2005

Recommend & Share

Related Content

A Simple, Mild, Catalytic, Enantioselective Addition of Terminal Acetylenes to AldehydesJournal of the American Chemical Society
- A Simple, Mild, Catalytic, Enantioselective Addition of Terminal Acetylenes to Aldehydes
  Neel K. Anand and Erick M. Carreira
  Journal of the American Chemical Society 2001 123 (39), pp 9687–9688
  Abstract | Full Text HTML | Hi-Res PDF
Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic AnhydridesJournal of the American Chemical Society
- Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic Anhydrides
  Yasufumi Yoshino, Takuya Kurahashi and Seijiro Matsubara
  Journal of the American Chemical Society 2009 131 (22), pp 7494–7495
  Abstract: An intermolecular nickel-catalyzed addition reaction in which isatoic anhydrides react with alkynes to afford substituted quinolones has been developed. A mechanistic rationale is proposed, implying oxidative addition of Ni(0) to a carbamate, which allows ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Cyclocarboamination of Alkynes with Aziridines: Synthesis of 2,3-Dihydropyrroles by a Catalyzed Formal [3 + 2] CycloadditionJournal of the American Chemical Society
- Cyclocarboamination of Alkynes with Aziridines: Synthesis of 2,3-Dihydropyrroles by a Catalyzed Formal [3 + 2] Cycloaddition
  Paul A. Wender and Daniel Strand
  Journal of the American Chemical Society 2009 131 (22), pp 7528–7529
  Abstract: An efficient cyclocarboamination reaction of nonactivated alkynes with aziridines, catalyzed by Lewis or Bronsted acids, to form 2,3-dihydropyrroles through a formal [3+2] cycloaddition, is described. The reaction provides a wide range of polysubstituted ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Note

Me₂Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones