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Chemistry Thesis

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Elisabeth Young

on 3 May 2013

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Transcript of Chemistry Thesis

Future - finish a synthesis of the desired ligand
- complex ligand to Iron Center
- test for catalytic activity and hydrogenation reactions Catalysis Development of Iron-Based Catalysts
for the Homogeneous Hydrogenation of C=X and C=X Ligand Synthesis 1st Approach - simple method, known for related compounds** Ullman Reaction (3rd Approach) - another type of cross-coupling, usually performed at high temperature Suzuki Cross-Coupling (2nd Approach) - known to be effective for forming bipyridines Metal
Complexing Dioxide Bipyridine - clearly no Bipyridine
- symmetric molecule
- clean Lit mp: 297C
Experimental mp:289C H-NMR H-NMR revealed a complex mixture and the decision was made it proceed with reaction. Borate intermediate was synthesized according to Billingsley and Buckwald. Corresponded with mp and H-NMR literature values provided Why Asymmetric Hydrogenation Problem - Analysis by H-NMR revealed a complex mixture
- Intended ligand was not the major product
*Billingsley, K.L. and Buckwald, S.l. 2008. A General and Efficient Method for the Suzuki–Miyaura Coupling of 2-Pyridyl Nucleophiles. Angewandte Chemistry International Edition. 47: 4695 –4698. * IR (KBr pellet, cm-1)
3096 (w)
1600 (s)
1424 (s)
1389 (s). Solution Objective

- >1,000,000 TON (turnover number, measure of catalyst productivity)

- 79% enantiomeric selection

- 40% reduction in application mass Toxicity My Focus Ultimate Goal a. synthesis of complex 1
b. test in hydrogenation reactions a. synthesis of hydroxy bipyridine
b. attach to metal center Possible Impurity Fe < $0.10/mol - H-NMR revealed peaks analogous to starting material
- Should adjust conditions and utilize fresher solvents in future experiments
- Would be most efficient method
- want to attached ligand to metal center similar to Pandrey in Synthesis of Some Novel Iodo(n-cyclopentadienyl)-iron Di-amine Complexes


- Completed to model two reactions with ligands: ethylene diamine and bipyridine


- immediate color change and formation of solid ee 80% ee 80% Scheme 1. Synthesis of Metolachor Basic Mechanics of Asymmetric Homogenous Hydrogenation V.N. Pandey. 1977. Synthesis of Some Novel Iodo(n-cyclopentadienyl)-iron Di-amine Complexes. Inorganica Chimica Acta, 25:L37-L38. *P.G. Simpson, A. Vinciguerra, and J.V. Quagino. 1962. The Donor Properties of 2, 2' Bipyridine N,N' Dioxide. Inorganic Chemistry 2(2):282-286.
**D.B. Morgan, G.O. Morton, and J.D. Albright. 1986. Synthesis of Heterolytic Chemistry 23: 1071-1077. S. Zhang, D. Zhang, and L.s> Liesbeskind. 1997. Ambient Temperature, Ullmann-like REductive Coupling of Aryl, Heteroaryl, and Alkenyl Halides. Journal of Organic Chemistry 62: 2312-2313. ? Time Savings
Cost Reduction
Reduction of Waste FASTER REACTIONS Time Savings
Cost Reduction
Reduction of Waste Shvo's Catalyst Casey's Catalyst - did not maintain reactivity of Shvo's Catalyst
- high activity for ketones, aldehydes, diketones, and imines. - Various attempts, but by H-NMR we were unable to distinguish our product
Results
benzene
4h benzene
4h benzene 4h Scheme 2. Mechanism of Ligand Assisted Heterolytic Cleavage of dihydrogen
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