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Organometallic Nickel(II) Phosphine Complexes for Suzuki-Miyaura Cross-Coupling; A Greener Alternative?

Organometallic Nickel(II) Phosphine Complexes for Suzuki-Miyaura Cross-Coupling; A Greener Alternative?
Contributors
Jason Cooke
Inorganic Chemistry Laboratory Coordinator | University of Alberta
John De Backere
Assistant Professor, Teaching Stream | University of Toronto, St. George Campus
Beyond Benign
Beyond Benign, Inc.
Learning Objets
Summary
In this experiment, students perform a Grignard reaction under air-free conditions to synthesize and isolate organometallic Ni(II) phosphine complex(es) that are used as pre-catalysts for a Suzuki-Miyaura Coupling reaction in tert-amyl alcohol.
Keyword Tags
Synthesis
Organometallics
Catalysis
Upper-Division Undergraduate
File (PDF, PPT, image, etc)
ni_suzukimiyaura_experiment_2023_08_29_final.docx
Digital Object Identifier (DOI)
https://doi.org/10.59877/YIPZ9200
Learning Goals/Student Objectives
In performing this experiment, a student will gain an appreciation for…
● Synthesis of organometallic complexes (air sensitive, phosphines, and Grignard reactions)
● Suzuki-Miyaura Cross-Coupling (C-C bond forming reactions)
● Catalysis (pre-catalysts, mechanisms, conditions, metrics, and optimization)
● Heteronuclear NMR (31P{1H} NMR for isolated Ni-compounds and 19F{1H} NMR for identification & quantification of in situ product formation. 1H also optional)
● Green chemistry considerations (greener solvents, metrics, energy efficiency)
Object Type
Laboratory experiment
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Collaborative/cooperative learning
Context-based learning
Hands-on learning
Green Chemistry Principles
Waste Prevention
Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Catalysis
Safety Precautions, Hazards, and Risk Assessment
Nickel(II) compounds are toxic if ingested, are skin and eye irritants, and some are suspected carcinogens. Tetrahydrofuran is a moderate to severe eye and respiratory irritant. Mesityl magnesium bromide solutions in tetrahydrofuran are flammable, corrosive, and react violently with water; the substance is also a suspected carcinogen.
Anhydrous potassium phosphate is corrosive, and care should be taken to avoid inhaling the fine powder – weigh this reagent in the fume hood. Phenylboronic acid and 1-bromo-4-(trifluoromethyl)benzene are irritants. 2 Methyl-butan-2-ol (tert-amyl alcohol) is an eye and skin irritant that is harmful if ingested.
Wear gloves and work in the fume hood throughout.
Teacher Recommendations or Piloting Data (if available)
The experiment has been tested over many years by hundreds of students. Recommendations and piloting data are available in the learning object.

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Submitted by

Jason Cooke
Reviewed by
Sara K Madsen
Published on
Moderation state
Published
Collection
Greener Inorganic Labs
Time required (if applicable)
Flexible; two 3-hour lab periods suggested
Creative Commons License
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.