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 › peer-review

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

Bibliographical note

Funding Information:
We thank Dr. Christopher Schwartz for assistance in analysis of 1H NMR spectral data for 2b, and Mark Raths of Willie's SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF?MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds.

Funding Information:
We thank Dr. Christopher Schwartz for assistance in analysis of 1 H NMR spectral data for 2b , and Mark Raths of Willie’s SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF–MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University.

Funding Information:
This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds .

Keywords

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

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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 › peer-review

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

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.",

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

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

note = "Funding Information: We thank Dr. Christopher Schwartz for assistance in analysis of 1H NMR spectral data for 2b, and Mark Raths of Willie's SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF?MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds. Funding Information: We thank Dr. Christopher Schwartz for assistance in analysis of 1 H NMR spectral data for 2b , and Mark Raths of Willie{\textquoteright}s SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF–MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. Funding Information: This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds . ",

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T2 - Synthesis, X-ray and computational studies

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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PY - 2020/4/1

Y1 - 2020/4/1

N2 - 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.

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.

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KW - Chiral ligands

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KW - NBO analysis

KW - Organometallic synthesis

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