1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies

Joseph Alia; Nancy E. Carpenter; Amanda J. Albrecht; Sharon Alexander; Taylir L. Bullick; Andrew J. Helmin; Scott A. Hubers; Daron E. Janzen; Jordan T. Koehn; Bethany Nyland; Laura Thoma; Lynn Weyer; Josh Wurst; Benjamin E. Kucera

doi:10.1016/j.poly.2020.114378

1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies

Joseph Alia, Nancy E. Carpenter, Amanda J. Albrecht, Sharon Alexander, Taylir L. Bullick, Andrew J. Helmin, Scott A. Hubers, Daron E. Janzen, Jordan T. Koehn, Bethany Nyland, Laura Thoma, Lynn Weyer, Josh Wurst, Benjamin E. Kucera

Research output: Contribution to journal › Article

Abstract

Advanced precursors to novel ferrocene-based ligands Cp₂FeC(O)CH(R)C(O)CH₃ (R = benzyl, allyl) were synthesized from 1-ferrocenylbutane-1,3-dione via active methylene chemistry. Crystal structures were obtained and computational studies carried out to explore the structural features of these new compounds. Addition of carbonyl electrophiles resulted in the formation of unexpected products, which were identified and mechanisms for their formation proposed.

Original language	English (US)
Article number	114378
Journal	Polyhedron
Volume	180
DOIs	https://doi.org/10.1016/j.poly.2020.114378
State	Published - Apr 1 2020

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Keywords

Alkylation
Butane-1,3-dione
Chiral ligands
Ferrocene
NBO analysis
Organometallic synthesis
Retro-Claisen

Cite this

Alia, J., Carpenter, N. E., Albrecht, A. J., Alexander, S., Bullick, T. L., Helmin, A. J., Hubers, S. A., Janzen, D. E., Koehn, J. T., Nyland, B., Thoma, L., Weyer, L., Wurst, J., & Kucera, B. E. (2020). 1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies. Polyhedron, 180, [114378]. https://doi.org/10.1016/j.poly.2020.114378

1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands : Synthesis, X-ray and computational studies. / Alia, Joseph; Carpenter, Nancy E.; Albrecht, Amanda J.; Alexander, Sharon; Bullick, Taylir L.; Helmin, Andrew J.; Hubers, Scott A.; Janzen, Daron E.; Koehn, Jordan T.; Nyland, Bethany; Thoma, Laura; Weyer, Lynn; Wurst, Josh; Kucera, Benjamin E.

In: Polyhedron, Vol. 180, 114378, 01.04.2020.

Research output: Contribution to journal › Article

Alia, Joseph ; Carpenter, Nancy E. ; Albrecht, Amanda J. ; Alexander, Sharon ; Bullick, Taylir L. ; Helmin, Andrew J. ; Hubers, Scott A. ; Janzen, Daron E. ; Koehn, Jordan T. ; Nyland, Bethany ; Thoma, Laura ; Weyer, Lynn ; Wurst, Josh ; Kucera, Benjamin E. / 1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands : Synthesis, X-ray and computational studies. In: Polyhedron. 2020 ; Vol. 180.

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abstract = "Advanced precursors to novel ferrocene-based ligands Cp2FeC(O)CH(R)C(O)CH3 (R = benzyl, allyl) were synthesized from 1-ferrocenylbutane-1,3-dione via active methylene chemistry. Crystal structures were obtained and computational studies carried out to explore the structural features of these new compounds. Addition of carbonyl electrophiles resulted in the formation of unexpected products, which were identified and mechanisms for their formation proposed.",

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AU - Alia, Joseph

AU - Carpenter, Nancy E.

AU - Albrecht, Amanda J.

AU - Alexander, Sharon

AU - Bullick, Taylir L.

AU - Helmin, Andrew J.

AU - Hubers, Scott A.

AU - Janzen, Daron E.

AU - Koehn, Jordan T.

AU - Nyland, Bethany

AU - Thoma, Laura

AU - Weyer, Lynn

AU - Wurst, Josh

AU - Kucera, Benjamin E.

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AB - Advanced precursors to novel ferrocene-based ligands Cp2FeC(O)CH(R)C(O)CH3 (R = benzyl, allyl) were synthesized from 1-ferrocenylbutane-1,3-dione via active methylene chemistry. Crystal structures were obtained and computational studies carried out to explore the structural features of these new compounds. Addition of carbonyl electrophiles resulted in the formation of unexpected products, which were identified and mechanisms for their formation proposed.

KW - Alkylation

KW - Butane-1,3-dione

KW - Chiral ligands

KW - Ferrocene

KW - NBO analysis

KW - Organometallic synthesis

KW - Retro-Claisen

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DO - 10.1016/j.poly.2020.114378

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Access

10.1016/j.poly.2020.114378