DOI: 10.1002/ange.200352635. Iron‐Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide

Iron‐Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide

10.1002/ange.200352635

Crossref journal-article

Wiley

Angewandte Chemie (311)

Bibliography

Legros, J., & Bolm, C. (2003). IronâCatalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide. Angewandte Chemie, 115(44), 5645â5647. Portico.

Authors 2

Julien Legros (first)
Carsten Bolm (additional)

References 38 Referenced 77

{'key': 'e_1_2_4_2_2', 'first-page': '38', 'volume': '24', 'author': 'Sheldon R. A.', 'year': '1994', 'journal-title': 'Chem. Tech.'} / Chem. Tech. by Sheldon R. A. (1994)
10.1002/(SICI)1521-3757(19990401)111:7<957::AID-ANGE957>3.0.CO;2-L
10.1002/(SICI)1521-3773(19990401)38:7<907::AID-ANIE907>3.0.CO;2-#
10.1016/S0040-4020(02)00440-4
10.1021/cen-v081n047.p019
For overviews on the use of H2O2in oxidation reactions see:
{'key': 'e_1_2_4_7_2', 'volume-title': 'Catalytic Oxidations with Hydrogen Peroxide as Oxidant', 'year': '1992'} / Catalytic Oxidations with Hydrogen Peroxide as Oxidant (1992)
10.1039/9781847550132
10.1021/cr020471z
10.1002/9783527619399.ch5m
10.1002/0471721506.ch10
{'key': 'e_1_2_4_13_2', 'first-page': '697', 'volume-title': 'Comprehensive Asymmetric Catalysis', 'author': 'Bolm C.', 'year': '1999'} / Comprehensive Asymmetric Catalysis by Bolm C. (1999)
Recently niobium and tungsten complexes have also been involved in asymmetric sulfoxidation reactions:
{'key': 'e_1_2_4_15_2', 'first-page': '1046', 'author': 'Miyazaki T.', 'year': '2003', 'journal-title': 'Synlett'} / Synlett by Miyazaki T. (2003)
10.1016/S0957-4166(02)00865-0
10.1021/jo00298a046
10.1039/C39900001378
10.1016/S0957-4166(00)86106-6
10.1039/c39920000254
10.1016/0304-5102(92)80030-K
For an exception see references [7 b c]. In these cases Naruta et al. reported that the oxidation of methyl pentafluorophenyl sulfide gave a product with 73 %ee.
10.1016/S0040-4039(97)00710-7
10.1002/1521-3765(20020301)8:5<1196::AID-CHEM1196>3.0.CO;2-Z
Such ligands have also been used in vanadium‐catalyzed asymmetric sulfide oxidations; see:
10.1002/ange.19951072317
10.1002/anie.199526401
10.1016/S1381-1169(96)00359-7
10.1055/s-1998-1948
10.1055/s-2002-32582
10.1021/jo0205560
10.1021/ol034254b
10.1016/S0010-8545(02)00249-7
Urea–H2O2adduct (UHP) also gives satisfactory results.
After a reaction time of 16 h a potassium iodide test revealed that no more oxidant was present in the reaction medium. In the presence of a large excess of H2O2 complete conversion of sulfide into racemic sulfoxide and sulfone was observed. In independent experiments it was demonstrated that the sulfoxide to sulfone oxidation proceeded in a non‐enantioselective manner.
Attempts to substitute dichloromethane with other solvents such as acetonitrile acetone toluene ortert‐butyl methyl ether were unsuccessful.

Dates

Type	When
Created	21 years, 9 months ago (Nov. 12, 2003, 10 a.m.)
Deposited	1 year, 10 months ago (Oct. 11, 2023, 9:20 a.m.)
Indexed	1 year, 9 months ago (Nov. 17, 2023, 12:30 a.m.)
Issued	21 years, 9 months ago (Nov. 11, 2003)
Published	21 years, 9 months ago (Nov. 11, 2003)
Published Online	21 years, 9 months ago (Nov. 11, 2003)
Published Print	21 years, 9 months ago (Nov. 17, 2003)

Funders 0

None

BibTeX

@article{Legros_2003, title={Iron‐Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide}, volume={115}, ISSN={1521-3757}, url={http://dx.doi.org/10.1002/ange.200352635}, DOI={10.1002/ange.200352635}, number={44}, journal={Angewandte Chemie}, publisher={Wiley}, author={Legros, Julien and Bolm, Carsten}, year={2003}, month=nov, pages={5645–5647} }

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