Prev. Article Next Article Table of Contents

Note

Expanding the Scope of Lewis Acid Catalysis in Water: Remarkable Ligand Acceleration of Aqueous Ytterbium Triflate Catalyzed Michael Addition Reactions

Supporting Info

Rui Ding, Kambiz Katebzadeh, Lisa Roman, Karl-Erik Bergquist, and Ulf M. Lindström*

Department of Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden ulf.lindstrom@organic.lu.se

J. Org. Chem., 2006, 71 (1), pp 352–355

DOI: 10.1021/jo051540n

Publication Date (Web): December 6, 2005

To whom correspondence should be addressed. Fax: (+46) 46 2228209.

Abstract

Significant rate acceleration of metal-catalyzed Michael addition reactions in water was observed upon addition of small, dibasic ligands. Ytterbium triflate and TMEDA was the most effective combination leading to a nearly 20-fold faster reaction than in the absence of ligand.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 06, 2006
Received July 24, 2005

Recommend & Share

Related Content

Organic Reactions on Silica in WaterChemical Reviews
- Organic Reactions on Silica in Water
  Satoshi Minakata and Mitsuo Komatsu
  Chemical Reviews 2009 109 (2), pp 711–724
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
FeCl₃-Catalyzed 1,2-Addition Reactions of Aryl Aldehydes with Arylboronic AcidsOrganic Letters
- FeCl₃-Catalyzed 1,2-Addition Reactions of Aryl Aldehydes with Arylboronic Acids
  Tao Zou, Sha-Sha Pi and Jin-Heng Li
  Organic Letters 2009 11 (2), pp 453–456
  Abstract: A novel protocol for the 1,2-addition reactions of electron-deficient aryl aldehydes with arylboronic acids using an inexpensive and environmentally benign iron catalyst is reported. In the presence of FeCl₃ and 2-(di-tert-butylphosphino)biphenyl, 1,2-...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Asymmetric, Catalytic, and Direct Self-Aldol Reaction of Acetaldehyde Catalyzed by DiarylprolinolOrganic Letters
- Asymmetric, Catalytic, and Direct Self-Aldol Reaction of Acetaldehyde Catalyzed by Diarylprolinol
  Yujiro Hayashi, Sampak Samanta, Takahiko Itoh and Hayato Ishikawa
  Organic Letters 2008 10 (24), pp 5581–5583
  Abstract: An asymmetric, catalytic, and direct self-aldol reaction of acetaldehyde was catalyzed by diarylprolinol in NMP, affording the trimer acetal, which was generated by the reaction of the self-aldol product with another acetaldehyde molecule in a moderate ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Note

Expanding the Scope of Lewis Acid Catalysis in Water: Remarkable Ligand Acceleration of Aqueous Ytterbium Triflate Catalyzed Michael Addition Reactions