Development of environmentally benign catalytic dehydration process

Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

More environmentally benign alternatives to current chemical processes, especially large-scale fundamental reactions, are highly desirable for many reactions. We have developed bulky diary-lammonium pentafluorobenzenesulfonates 1a and 2a as mild and extremely active dehydration catalysts. In the presence of the catalysts, dehydrative cyclization of 1,3,5-triketones and ester condensation of carboxylic acids with equimolar amounts of alcohols are performed in heptane by heating at 80 °C without the removal of water. We have also developed an efficient molybdenum oxide-catalyzed dehydrative cyclization of serine, threonine, and cysteine derivatives, which gives oxazolines and thiazolies. In the presence of molybdenum oxides, the reaction is carried out by heating at azeotropic reflux with the removal of water. Phosphate monoesters are synthesized from a mixture of phosphoric acid and alcohols in the presence of tributylamine. The reaction is promoted by nucleophilic bases such as N-butylimidazole. The hydroxyl groups of amino alcohols, such as 5′-hydroxyl group of 2′, 3′-O-isopropylidene ribonucleosides, are phosphorylated selectively.

Original languageEnglish
Pages (from-to)651-663
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume64
Issue number6
Publication statusPublished - Jun 2006
Externally publishedYes

Fingerprint

Molybdenum oxide
Cyclization
Dehydration
Hydroxyl Radical
Alcohols
Amino Alcohols
Ribonucleosides
Heating
Heptanes
Catalysts
Water
Threonine
Carboxylic Acids
Serine
Cysteine
Condensation
Esters
Phosphates
Derivatives
propylene

Keywords

  • γ-pyrone
  • Ammonium sulfonate
  • Catalytic dehydration
  • Ester condensation
  • Hydrophobic effect
  • Molybdenum oxide
  • Nucleophilic base
  • Oxazoline
  • Phosphate monoester
  • Thiazoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Development of environmentally benign catalytic dehydration process. / Sakakura, Akira; Ishihara, Kazuaki.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 64, No. 6, 06.2006, p. 651-663.

Research output: Contribution to journalArticle

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