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Article

New Chiral Phosphoramidite Complexes of Iron as Catalytic Precursors in the Oxidation of Activated Methylene Groups

1
University of Missouri - St. Louis, Department of Chemistry and Biochemistry, One University Boulevard, St. Louis, MO 63121, USA
2
Department of Chemistry and Biochemistry and Center for Nanoscience, University of Missouri - St. Louis, One University Boulevard, St. Louis, MO 63121, USA
*
Author to whom correspondence should be addressed.
Molecules 2010, 15(4), 2631-2650; https://doi.org/10.3390/molecules15042631
Received: 21 February 2010 / Revised: 31 March 2010 / Accepted: 6 April 2010 / Published: 12 April 2010
(This article belongs to the Special Issue Organometallic Chemistry)
New phosphoramidite complexes of iron were synthesized and structurally characterized. Reaction of the known chiral phosphoramidites (RO)2PNR’2 (R = binaphthyl, R’ = CH3, 1a; R = binaphthyl, R’ = benzyl, 1b) with [FeBr(Cp)(CO)2] afforded the title compounds [FeBr(Cp)(CO)(1a,b)] (4a,b) in 34 and 65 % isolated yields as mixtures of diastereomers, since both the metal and the ligand are stereogenic. Similarly, reaction of 1b with [Fe(Cp)I(CO)2] in the presence of catalytic [Fe(Cp)(CO)2]2 afforded [Fe(Cp)I(CO)(1b)] (5b) in 81% yield as a mixture of diastereomers. The molecular structures of 4a, 4b and 5 were determined, revealing a pseudo octahedral coordination geometry about the iron center. The new metal complexes are catalytically active in the oxidation of benzylic methylene groups to the corresponding ketones, utilizing t-BuOOH as oxidant (2 mol% catalyst, 36 h, room temperature, 31−80% yield). View Full-Text
Keywords: iron; phosphoramidites; X-ray; chiral at metal; benzylic oxidations iron; phosphoramidites; X-ray; chiral at metal; benzylic oxidations
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MDPI and ACS Style

Shejwalkar, P.; Rath, N.P.; Bauer, E.B. New Chiral Phosphoramidite Complexes of Iron as Catalytic Precursors in the Oxidation of Activated Methylene Groups. Molecules 2010, 15, 2631-2650. https://doi.org/10.3390/molecules15042631

AMA Style

Shejwalkar P, Rath NP, Bauer EB. New Chiral Phosphoramidite Complexes of Iron as Catalytic Precursors in the Oxidation of Activated Methylene Groups. Molecules. 2010; 15(4):2631-2650. https://doi.org/10.3390/molecules15042631

Chicago/Turabian Style

Shejwalkar, Pushkar, Nigam P. Rath, and Eike B. Bauer. 2010. "New Chiral Phosphoramidite Complexes of Iron as Catalytic Precursors in the Oxidation of Activated Methylene Groups" Molecules 15, no. 4: 2631-2650. https://doi.org/10.3390/molecules15042631

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