What question did this study set out to answer?

To synthesize pentaphenylferrocenyl di-tert-butylphosphine and evaluate its performance and stability in palladium-catalyzed carbon-carbon, carbon-nitrogen, and carbon-oxygen bond-forming reactions.

July 4, 2002The Journal of Organic Chemistry

Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings

View Full Paper

Ask AI

Bookmark

Authors

NKNoriyasu KataokaSuzuki (Japan)QSQuinetta D. ShelbyDePaul University JSJames P. StambuliAbbVie (United States)

Discussion

Member takes

Overview

Synthetic investigation demonstrates versatile palladium-catalyzed cross-couplings using air-stable ferrocenyl phosphines, highlighting a general route for carbon-heteroatom bond formation.

Key Points

To synthesize pentaphenylferrocenyl di-tert-butylphosphine and evaluate its performance and stability in palladium-catalyzed carbon-carbon, carbon-nitrogen, and carbon-oxygen bond-forming reactions.
Synthesized pentaphenylferrocenyl di-tert-butylphosphine in high yield via a two-step synthetic sequence.
Evaluated catalytic cross-coupling efficiency across aminations, Suzuki couplings, and aryl ether formations using electron-rich and electron-poor aryl bromides and chlorides.
Tested reaction tolerance with primary and secondary amines, terminal alkylboronic acids without toxic bases, and determined aerobic stability in solid and solution states.
Observed catalyst turnovers of roughly 1000 for aryl halide aminations involving unactivated aryl bromides or chlorides.
Achieved successful couplings of aryl halides with cyclic or acyclic secondary amines, primary amines, and terminal alkylboronic acids under mild conditions.
Demonstrated air stability of both the free ligand and its palladium(0) complexes in the solid state, alongside slow oxygen reactivity in solution.

Cite This Study

Kataoka et al. (2002) studied this question.

synapsesocial.com/papers/6a1078cbe1a472cb5efcf7e6 https://doi.org/10.1021/jo025732j

View Full Paper

Ask AI

Bookmark

July 4, 2002The Journal of Organic Chemistry

Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings

View Full Paper

Ask AI

Bookmark

Authors

NKNoriyasu KataokaSuzuki (Japan)QSQuinetta D. ShelbyDePaul University JSJames P. StambuliAbbVie (United States)

Discussion

Member takes

Overview

Synthetic investigation demonstrates versatile palladium-catalyzed cross-couplings using air-stable ferrocenyl phosphines, highlighting a general route for carbon-heteroatom bond formation.

Key Points

To synthesize pentaphenylferrocenyl di-tert-butylphosphine and evaluate its performance and stability in palladium-catalyzed carbon-carbon, carbon-nitrogen, and carbon-oxygen bond-forming reactions.
Synthesized pentaphenylferrocenyl di-tert-butylphosphine in high yield via a two-step synthetic sequence.
Evaluated catalytic cross-coupling efficiency across aminations, Suzuki couplings, and aryl ether formations using electron-rich and electron-poor aryl bromides and chlorides.
Tested reaction tolerance with primary and secondary amines, terminal alkylboronic acids without toxic bases, and determined aerobic stability in solid and solution states.
Observed catalyst turnovers of roughly 1000 for aryl halide aminations involving unactivated aryl bromides or chlorides.
Achieved successful couplings of aryl halides with cyclic or acyclic secondary amines, primary amines, and terminal alkylboronic acids under mild conditions.
Demonstrated air stability of both the free ligand and its palladium(0) complexes in the solid state, alongside slow oxygen reactivity in solution.

Cite This Study

Kataoka et al. (2002) studied this question.

synapsesocial.com/papers/6a1078cbe1a472cb5efcf7e6 https://doi.org/10.1021/jo025732j

Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

View Full Paper

Ask AI

Bookmark