Title

Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations

Student Authors

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

Document Type

Article

Publication Date

3-27-2018

Department

Chemistry

Abstract

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.

Comments

The Supporting Information is also available free of charge on the ACS Publications website at DOI: 10.1021/acs.organomet.8b00037.

DOI

10.1021/acs.organomet.8b00037

Required Publisher's Statement

The article is available online from the publisher's website: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00037

This item is not available in The Cupola.

Additional Files

supporting material.pdf (2918 kB)

Share

COinS