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

Chemistry (Morris)

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

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Publisher Copyright:
© 2020 Elsevier Ltd

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, Article 114378. https://doi.org/10.1016/j.poly.2020.114378

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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 = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = apr,

day = "1",

doi = "10.1016/j.poly.2020.114378",

language = "English (US)",

volume = "180",

journal = "Polyhedron",

issn = "0277-5387",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - 1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands

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.

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.

KW - Alkylation

KW - Butane-1,3-dione

KW - Chiral ligands

KW - Ferrocene

KW - NBO analysis

KW - Organometallic synthesis

KW - Retro-Claisen

UR - http://www.scopus.com/inward/record.url?scp=85078993324&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85078993324&partnerID=8YFLogxK

U2 - 10.1016/j.poly.2020.114378

DO - 10.1016/j.poly.2020.114378

M3 - Article

AN - SCOPUS:85078993324

SN - 0277-5387

VL - 180

JO - Polyhedron

JF - Polyhedron

M1 - 114378

ER -

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

Abstract

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Keywords

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