Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations
Andrew R. Mahoney '17, Gettysburg College
Rebecca A. Sponenburg '14, Gettysburg College
Kathryn P. Zimmerman '16, Gettysburg College
Daniel K. Kim '12, Gettysburg College
Emily E. Harrison '18, Gettysburg College
Four (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds were synthesized, and their activities in transfer hydrogenations of carbonyl compounds and transfer dehydrogenations of alcohols were explored and compared to those of the well-established [2,5-(SiMe3)2-3,4-(CH2)4(η4-C4C═O)]Fe(CO)3 (3). A new compound, [2,5-bis(3,5-dimethylphenyl)-3,4-diphenylcyclopentadienone]iron tricarbonyl (7), was the most active catalyst in both transfer hydrogenations and dehydrogenations, and compound 3 was the least active catalyst in transfer hydrogenations. Evidence was found for product inhibition of both 3 and 7 in a transfer dehydrogenation reaction, with the activity of 3 being more heavily affected. A monomeric iron hydride derived from 7 was spectroscopically observed during a transfer hydrogenation, and no diiron bridging hydrides were found under reductive or oxidative conditions. Initial results in the transfer hydrogenation of N-benzylideneaniline showed that 3 was a significantly less active catalyst in comparison to the (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds.
Funk, Timothy W., Andrew R. Mahoney, Rebecca A. Sponenburg, Kathryn P. Zimmerman, Daniel K. Kim, and Emily E. Harrison. "Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations." Organometallics 37, no. 7 (2018): 1133-1140.
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The article is available online from the publisher's website: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00037