Green asymmetric oxidation using air as oxidant

Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We found that (NO)- and (aqua)ruthenium-salen complexes are efficient catalysts for the asymmetric aerobic oxygen atom transfer reactions such as epoxidation and sulfoxidation at ambient temperature. (NO) ruthenium-salen complexes 2 and 3 could catalyze oxidation of sulfides and the epoxidation of conjugated olefins with good to high enantioselectivity using dioxygen as oxidant, albeit under visible light-irradiation, respectively. On the other hand, (aqua)ruthenium-salen complex 5 was found to catalyze highly enantioselective epoxidation in air even without irradiation. Although the mechanism of this ruthenium-catalyzed aerobic oxidation has not been completely elucidated, water that is bound to the ruthenium ion has been considered to play a critical role in proton coupled electron transfer, a key step for oxygen activation, and to be regenerated via oxo-hydroxo tautomerization. We also found that (di-μ-hydroxo)iron-salan complexes catalyzes asymmetric dehydrogenative oxidation reactions such as 2-naphthol coupling, alcohol oxidation, and dearomatization, using air as oxidant.

Original languageEnglish
Pages (from-to)1126-1135
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume71
Issue number11
DOIs
Publication statusPublished - Dec 1 2013

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Ruthenium
Oxidants
Epoxidation
Oxidation
Air
Oxygen
Irradiation
Enantioselectivity
Alkenes
Sulfides
Protons
Iron
Chemical activation
Alcohols
Ions
Atoms
Catalysts
Electrons
Water
disalicylaldehyde ethylenediamine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Green asymmetric oxidation using air as oxidant. / Uchida, Tatsuya; Katsuki, Tsutomu.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 71, No. 11, 01.12.2013, p. 1126-1135.

Research output: Contribution to journalArticle

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