Abstract: Molybdenum-Catalyzed Reduction of Amides to Amines: The Mechanism Unravelled (2011 SACNAS National Conference)

Thursday, October 27, 2011: 7:05 PM

Room C1/C2 (San Jose Convention Center)

Renzo Arias Ugarte, Ph.D Student , Chemistry, University Of Texas At El Paso, El Paso, TX

Eduardo Cervantes, Undergraduate , Chemistry, University Of Texas At El Paso, El Paso, TX

Hemant Sharma, Ph.D , Chemistry, University Of Texas At El Paso, El Paso, TX

Keith Pannell, Ph.D , Chemistry, University Of Texas At El Paso, El Paso, TX

We recently reported the photochemical irradiation of tertiary silanes, R₃SiH, to form symmetrical disiloxanes, R₃SiOSiR₃, using catalytic amounts of molybdenum and iron alkyl complexes (η⁵-C₅H₅)M(CO)_nMe, M = Fe, n = 2 (1); M = Mo, n = 3 (2), in the presence of DMF solvent . We suggested a mechanism in which R₃SiOCH₂NMe₂intermediates were formed and further reacted with R₃SiH to form siloxanes. We have extended this study for the synthesis of these intermediates, R₃SiOCH₂NMe₂, using molybdenum carbonyl complexes of the type: Mo(CO)₅L (L = CO, NMe₃) as a catalyst in the presence of DMF.

The new siloxymethylamines are shown to further react with R₃SiH, but only in the presence of the metal catalyst. This methodology represents a new synthetic approach for the synthesis of these derivatives R₃SiOCH₂NMe₂ and sheds light on the important reduction of amides to amines._.Full synthetic and characterization details of these new synthetic materials will be presented at the conference.

This research was supported by the Robert Welch Foundation (Grant AH-0546), Houston, TX.