Prev. Article Next Article Table of Contents

Letter

Ytterbium Triflate-Promoted Tandem One-Pot Oxidation−Cannizzaro Reaction of Aryl Methyl Ketones

Massimo Curini,* Francesco Epifano, Salvatore Genovese, M. Carla Marcotullio, and Ornelio Rosati

Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Via del Liceo, 06123 Perugia, Italy

Org. Lett., 2005, 7 (7), pp 1331–1333

DOI: 10.1021/ol050125e

Publication Date (Web): March 1, 2005

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

, curmax@unipg.it

Abstract

Ytterbium triflate was shown to be an effective catalyst in promoting the synthesis of either isopropyl esters or free α-hydroxy-arylacetic acids from substituted aromatic glyoxals and aryl methyl ketones, respectively. The reaction to provide acids starting from differently substituted ketones was carried out by an environmentally friendly method using an aqueous medium as a solvent and giving the adducts in 78−99% yield without any further purification after the usual workup.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue March 31, 2005
Received January 20, 2005

Recommend & Share

Related Content

Room-Temperature Cannizzaro Reaction under Mild Conditions Facilitated by Magnesium Bromide Ethyl Etherate and TriethylamineOrganic Letters
- Room-Temperature Cannizzaro Reaction under Mild Conditions Facilitated by Magnesium Bromide Ethyl Etherate and Triethylamine
  M. Saeed Abaee, Roholah Sharifi, and Mohammad M. Mojtahedi
  Organic Letters 2005 7 (26), pp 5893–5895
  Abstract: A room-temperature convenient Cannizzaro reaction prompted by magnesium bromide ethyl etherate and triethylamine is described for smooth conversion of aromatic aldehydes into their respective alcohols and carboxylic acids. The methodology is applicable to ...
  Abstract | Full Text HTML | Hi-Res PDF
Efficient Lewis Acid Catalyzed Intramolecular Cannizzaro ReactionThe Journal of Organic Chemistry
- Efficient Lewis Acid Catalyzed Intramolecular Cannizzaro Reaction
  Albert E. Russell, Steven P. Miller, and James P. Morken
  The Journal of Organic Chemistry 2000 65 (24), pp 8381–8383
  Abstract | Full Text HTML | Hi-Res PDF
Synthesis of Carboxamides by LDA-Catalyzed Haller−Bauer and Cannizzaro ReactionsOrganic Letters
- Synthesis of Carboxamides by LDA-Catalyzed Haller−Bauer and Cannizzaro Reactions
  Kazuaki Ishihara and Takayuki Yano
  Organic Letters 2004 6 (12), pp 1983–1986
  Abstract: The first direct synthesis of N-alkylcarboxamides and N,N-dialkylcarboxamides by Haller−Bauer (HB) and Cannizzaro-type reactions has been realized. Lithium N,N-diisopropylamide (LDA) catalyst was successfully used in not only the HB reaction of benzylic ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Ytterbium Triflate-Promoted Tandem One-Pot Oxidation−Cannizzaro Reaction of Aryl Methyl Ketones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Room-Temperature Cannizzaro Reaction under Mild Conditions Facilitated by Magnesium Bromide Ethyl Etherate and Triethylamine

Efficient Lewis Acid Catalyzed Intramolecular Cannizzaro Reaction

Synthesis of Carboxamides by LDA-Catalyzed Haller−Bauer and Cannizzaro Reactions

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES