DeBrota M, Pflueger J - Studies of Cobalt Boride-Mediated Nitrile Reductions - Project Poster

Michael DeBrota
Michael DeBrotaMedical Student
Background
Studies of Cobalt Boride-Mediated Nitrile Reductions
Michael DeBrota and Jason J. Pflueger*
Rose-Hulman Institute of Technology, Terre Haute, Indiana
Optimization in Water Functional Group Compatibility
Conclusions
Acknowledgements
Solvent Screen
Other Parameters
• The nitrile is a versatile and robust functional group
• Nitrile reduction to the corresponding amine generally requires harsh
conditions with poor functional group tolerance (typically LiAlH4 or high
pressures of H2 gas)
• Satoh and coworkers reported the combination of cobalt(II) chloride and
sodium borohydride as an effective reducing agent for nitriles, nitro groups,
and amides1
• Ganem and coworkers isolated the cobalt boride (Co2B) formed in this
reaction and found borane tert-butylamine (BH3•tBuNH2) to be an effective
external reductant2
• These initial studies suggested possible selectivity for nitriles in the
presence of amides, esters, and alkenes with minimal follow-up work
performed
• Despite the broad synthetic potential for this reduction protocol, there has
only been one recent application in organic synthesis3
Goal: Develop a convenient, selective, high-yielding, functional group- tolerant
nitrile reduction protocol using cobalt boride
Future Directions
RHIT Department of Chemistry and Biochemistry
James (Lou) Johnson – Instrument Manager
Michelle Sharp – Stockroom Manager
Rose-Hulman Summer Undergraduate Research Fellowship (R-SURF)
Eli Lilly Undergraduate Research Grant
• Achieved mild and selective reduction of benzonitrile to benzyl alcohol
mediated by cobalt boride
• Water, a green solvent, used for both cobalt boride preparation and nitrile
reduction
• Cobalt boride showed no catalytic activity in this reaction
• Conditions compatible with several common functional groups
• Complete optimization of reaction conditions in water to produce alcohols
• Explore scope of aromatic nitrile substrates (electronics, substitution pattern,
functional group tolerance, presence of heteroatoms)
• Expand reaction conditions to aliphatic nitrile reduction
• Investigate conditions for selective reduction to the corresponding primary
amine (aromatic, heteroaromatic, and aliphatic nitriles)
1) Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Tetrahedron Lett. 1969, 52, 4555-4558.
2) Heinzman, S. W.; Ganem, B. J. Am. Chem. Soc. 1982, 104, 6801-6802.
3) Kou, K. G. M.; Pflueger, J. J.; Kiho, T.; Morrill, L. C.; Fisher, E. L.; Clagg, K.; Lebold, T. P.; Kisunzu, J. K.;
Sarpong, R. J. Am. Chem. Soc. 2018, 140, 8105-8109.
• Protic solvents were the most effective, although some conversion was
observed in toluene at 100 °C
• THF mixtures with MeOH or H2O show promise for broader substrate
solubility
• The reaction also proceeded fully in pure water, producing a significant
amount of benzyl alcohol
• Potential for 1-step green alcohol synthesis from nitriles
Screening Alternative Reducing Agents
Assessing Catalytic Activity of Co2B
• Decreasing concentration led to increased proportion of alcohol
• Changing drying agent to Na2SO4 prevented protonation of amine product
• Decreasing equivalents of BH3•tBuNH2 greatly improved selectivity for
benzyl alcohol formation
1 de 1

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DeBrota M, Pflueger J - Studies of Cobalt Boride-Mediated Nitrile Reductions - Project Poster

  • 1. Background Studies of Cobalt Boride-Mediated Nitrile Reductions Michael DeBrota and Jason J. Pflueger* Rose-Hulman Institute of Technology, Terre Haute, Indiana Optimization in Water Functional Group Compatibility Conclusions Acknowledgements Solvent Screen Other Parameters • The nitrile is a versatile and robust functional group • Nitrile reduction to the corresponding amine generally requires harsh conditions with poor functional group tolerance (typically LiAlH4 or high pressures of H2 gas) • Satoh and coworkers reported the combination of cobalt(II) chloride and sodium borohydride as an effective reducing agent for nitriles, nitro groups, and amides1 • Ganem and coworkers isolated the cobalt boride (Co2B) formed in this reaction and found borane tert-butylamine (BH3•tBuNH2) to be an effective external reductant2 • These initial studies suggested possible selectivity for nitriles in the presence of amides, esters, and alkenes with minimal follow-up work performed • Despite the broad synthetic potential for this reduction protocol, there has only been one recent application in organic synthesis3 Goal: Develop a convenient, selective, high-yielding, functional group- tolerant nitrile reduction protocol using cobalt boride Future Directions RHIT Department of Chemistry and Biochemistry James (Lou) Johnson – Instrument Manager Michelle Sharp – Stockroom Manager Rose-Hulman Summer Undergraduate Research Fellowship (R-SURF) Eli Lilly Undergraduate Research Grant • Achieved mild and selective reduction of benzonitrile to benzyl alcohol mediated by cobalt boride • Water, a green solvent, used for both cobalt boride preparation and nitrile reduction • Cobalt boride showed no catalytic activity in this reaction • Conditions compatible with several common functional groups • Complete optimization of reaction conditions in water to produce alcohols • Explore scope of aromatic nitrile substrates (electronics, substitution pattern, functional group tolerance, presence of heteroatoms) • Expand reaction conditions to aliphatic nitrile reduction • Investigate conditions for selective reduction to the corresponding primary amine (aromatic, heteroaromatic, and aliphatic nitriles) 1) Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Tetrahedron Lett. 1969, 52, 4555-4558. 2) Heinzman, S. W.; Ganem, B. J. Am. Chem. Soc. 1982, 104, 6801-6802. 3) Kou, K. G. M.; Pflueger, J. J.; Kiho, T.; Morrill, L. C.; Fisher, E. L.; Clagg, K.; Lebold, T. P.; Kisunzu, J. K.; Sarpong, R. J. Am. Chem. Soc. 2018, 140, 8105-8109. • Protic solvents were the most effective, although some conversion was observed in toluene at 100 °C • THF mixtures with MeOH or H2O show promise for broader substrate solubility • The reaction also proceeded fully in pure water, producing a significant amount of benzyl alcohol • Potential for 1-step green alcohol synthesis from nitriles Screening Alternative Reducing Agents Assessing Catalytic Activity of Co2B • Decreasing concentration led to increased proportion of alcohol • Changing drying agent to Na2SO4 prevented protonation of amine product • Decreasing equivalents of BH3•tBuNH2 greatly improved selectivity for benzyl alcohol formation