Synthetic Factors Governing Access to Tris(β-diketimine) Cyclophanes versus Tripodal Tri-β-aminoenones

Mary C Eaton; Brian J Knight; Robin Brahmi; Ricardo B Ferreira; Vincent J Catalano; Arnold L Rheingold; Ion Ghiviriga; Leslie J Murray

doi:10.1021/acs.joc.0c01708

Synthetic Factors Governing Access to Tris(β-diketimine) Cyclophanes versus Tripodal Tri-β-aminoenones

J Org Chem. 2020 Nov 6;85(21):13579-13588. doi: 10.1021/acs.joc.0c01708. Epub 2020 Oct 27.

Authors

Mary C Eaton¹, Brian J Knight¹, Robin Brahmi¹, Ricardo B Ferreira¹, Vincent J Catalano², Arnold L Rheingold³, Ion Ghiviriga⁴, Leslie J Murray¹

Affiliations

¹ Center for Catalysis and Florida Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, 214 Leigh Hall, P.O. Box 117200, Gainesville, Florida 32611, United States.
² Department of Chemistry, University of Nevada, Reno, Nevada 89557, United States.
³ Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, San Diego, California 92093, United States.
⁴ Department of Chemistry, University of Florida, 214 Leigh Hall, P.O. Box 117200, Gainesville, Florida 32611, United States.

Abstract

Tris(β-diketimine) cyclophanes are an important ligand class for investigating cooperative multimetallic interactions of bioinorganic clusters. Discussed herein are the synthetic factors governing access to tris(β-diketimine) cyclophanes versus tripodal tri-β-aminoenones. Cyclophanes bearing Me, Et, and MeO cap substituents and β-Me, Et, or Ph arm substituents are obtained, and a modified condensation method produced α-Me β-Me cyclophane. These operationally simple procedures produce the ligands in gram quantities and in 22-94% yields.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Ligands*

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Ligands

Abstract

Publication types

MeSH terms

Substances

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